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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H22N6O
Molecular Weight 386.4497
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of IBRUTINIB N-DESACRYLOYL IMPURITY

SMILES

NC1=C2C(=NC=N1)N(N=C2C3=CC=C(OC4=CC=CC=C4)C=C3)[C@@H]5CCCNC5

InChI

InChIKey=GPSQYTDPBDNDGI-MRXNPFEDSA-N
InChI=1S/C22H22N6O/c23-21-19-20(15-8-10-18(11-9-15)29-17-6-2-1-3-7-17)27-28(22(19)26-14-25-21)16-5-4-12-24-13-16/h1-3,6-11,14,16,24H,4-5,12-13H2,(H2,23,25,26)/t16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H22N6O
Molecular Weight 386.4497
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

(R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine is a chemical precursor of BTK inhibitor ibrutinib and related compounds. (R)-3-(4-phenoxyphenyl)-1-(piperidin-3-yl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine lacks the propenamide group that is responsible for covalent binding to cysteine residue of BTK kinase.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Discovery of (R)-1-(3-(4-Amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)-2-(dimethylamino)ethanone (CHMFL-FLT3-122) as a Potent and Orally Available FLT3 Kinase Inhibitor for FLT3-ITD Positive Acute Myeloid Leukemia.
2015 Dec 24
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Jul 07 00:18:45 UTC 2023
Edited
by admin
on Fri Jul 07 00:18:45 UTC 2023
Record UNII
NR6GN4MC2R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
IBRUTINIB N-DESACRYLOYL IMPURITY
Common Name English
1H-PYRAZOLO(3,4-D)PYRIMIDIN-4-AMINE, 3-(4-PHENOXYPHENYL)-1-(3R)-3-PIPERIDINYL-
Common Name English
(R)-3-(4-PHENOXYPHENYL)-1-(PIPERIDIN-3-YL)-1H-PYRAZOLO(3,4-D)PYRIMIDIN-4-AMINE
Common Name English
Code System Code Type Description
PUBCHEM
58223272
Created by admin on Fri Jul 07 00:18:45 UTC 2023 , Edited by admin on Fri Jul 07 00:18:45 UTC 2023
PRIMARY
CAS
1022150-12-4
Created by admin on Fri Jul 07 00:18:45 UTC 2023 , Edited by admin on Fri Jul 07 00:18:45 UTC 2023
PRIMARY
FDA UNII
NR6GN4MC2R
Created by admin on Fri Jul 07 00:18:45 UTC 2023 , Edited by admin on Fri Jul 07 00:18:45 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> IMPURITY