(R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide → HCID 76901600, compound

HRID 62465Notes

Reaction equation

HRID 62465 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]2[N:13]([C@@H:35]3[CH2:43][CH2:42][CH2:41][C:40]4[N:39](S(C5C=CC(C)=CC=5)(=O)=O)[N:38]=[CH:37][C:36]3=4)[N:14]=[C:15]([C:16]3[CH:34]=[CH:33][C:19]([C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=4)=[O:21])=[CH:18][CH:17]=3)[C:8]=12>C(O)(C(F)(F)F)=O>[NH2:6][C:7]1[N:12]=[CH:11][N:10]=[C:9]2[N:13]([C@@H:35]3[CH2:43][CH2:42][CH2:41][C:40]4[NH:39][N:38]=[CH:37][C:36]3=4)[N:14]=[C:15]([C:16]3[CH:17]=[CH:18][C:19]([C:20]([NH:22][C:23]4[CH:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=4)=[O:21])=[CH:33][CH:34]=3)[C:8]=12

Participants

3

Reactant 1

HCID 90304124(R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide

Product 1

HCID 76901600HCID 76901600, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of (R)-4-(4-((2,4-dimethoxybenzyl)amino)-1-(1-tosyl-4,5,6,7-tetrahydro-1H-indazol-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-N-(4-(trifluoromethyl)pyridin-2-yl)benzamide (90 mg, 0.109 mmol) in TFA (3 mL) was stirred for 3 h at 100° C. Removed the solvent and purified by preparative HPLC to give the title compound (30 mg, yield 52.8%).

Workup

  1. customRemoved the solvent
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-4b8d06eb916a48c3ba85c5492f81550c
Source dataset
uspto-grants-2016_09
Patent number
US09446130B2

Reaction notes

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