4-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid → 4-(cyclopropylamino)-N-(1-((4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-6-methylisoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide

HRID 1750868Notes

Reaction equation

HRID 1750868 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][N:6]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[C:26]4[CH:25]=[CH:24][C:23]([CH3:27])=[C:22]([NH2:28])[C:21]=4[CH:20]=[CH:19][N:18]=3)=[CH:12][C:11]=2[C:29]([F:32])([F:31])[F:30])[CH2:5][CH2:4]1)[CH3:2].[CH:33]1([NH:36][C:37]2[C:38]3[S:45][CH:44]=[C:43]([C:46](O)=[O:47])[C:39]=3[N:40]=[CH:41][N:42]=2)[CH2:35][CH2:34]1>>[CH:33]1([NH:36][C:37]2[C:38]3[S:45][CH:44]=[C:43]([C:46]([NH:28][C:22]4[C:23]([CH3:27])=[CH:24][CH:25]=[C:26]5[C:21]=4[CH:20]=[CH:19][N:18]=[C:17]5[NH:16][C:13]4[CH:14]=[CH:15][C:10]([CH2:9][N:6]5[CH2:7][CH2:8][N:3]([CH2:1][CH3:2])[CH2:4][CH2:5]5)=[C:11]([C:29]([F:31])([F:30])[F:32])[CH:12]=4)=[O:47])[C:39]=3[N:40]=[CH:41][N:42]=2)[CH2:35][CH2:34]1

Participants

3

Reactant 2

HCID 673596884-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acidHCID 131733609N1-(4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl)-6-methyl-isoquinolin-1,5-diamine

Product 1

HCID 716227214-(cyclopropylamino)-N-(1-((4-((4-ethylpiperazin-1-yl)methyl)-3-(trifluoromethyl)phenyl)amino)-6-methylisoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamideYield 50.4%

Procedure

The procedures of <Step 3> of Example 1 were repeated in sequence, except for using N1-(4-(4-ethyl-piperazin-1-ylmethyl)-3-trifluoromethyl-phenyl)-6-methyl-isoquinolin-1,5-diamine (0.015 g, 0.03 mmol) and 4-cyclopropylamino-thieno[3,2-d]pyrimidine-7-carboxylic acid (see WO 2011009687, 0.04 mmol) to obtain the title compound (10 mg, 46%).

Sources & evidence

ORD record
ord-71f05afb39744a2cbec30e859cab5be3
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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