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

HRID 1750866Notes

Reaction equation

HRID 1750866 reaction equation
[NH2:1][C:2]1[C:3]2[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]3[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]4[C:15]=3[CH:16]=[CH:17][N:18]=[C:19]4[NH:25][C:26]3[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([N:36]4[CH:40]=[C:39]([CH3:41])[N:38]=[CH:37]4)[CH:27]=3)=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.[CH:42]1(NC2C3SC=C(C(O)=O)C=3N=CN=2)[CH2:44][CH2:43]1>>[CH:42]1([NH:1][C:2]2[C:3]3[S:10][CH:9]=[C:8]([C:11]([NH:13][C:14]4[C:23]([CH3:24])=[CH:22][CH:21]=[C:20]5[C:15]=4[CH:16]=[CH:17][N:18]=[C:19]5[NH:25][C:26]4[CH:31]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:29]=[C:28]([N:36]5[CH:40]=[C:39]([CH3:41])[N:38]=[CH:37]5)[CH:27]=4)=[O:12])[C:4]=3[N:5]=[CH:6][N:7]=2)[CH2:44][CH2:43]1

Participants

3

Reactant 2

HCID 673596884-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acidHCID 716227184-amino-N-(6-methyl-1-((3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)amino)isoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamide

Product 1

HCID 716227194-(cyclopropylamino)-N-(6-methyl-1-((3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)phenyl)amino)isoquinolin-5-yl)thieno[3,2-d]pyrimidine-7-carboxamideYield 57%

Procedure

The procedures of <Step 3> of Example 1 were repeated, except for using 6-methyl-N1-(3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-phenyl)-isoquinolin-1,5-diamine (0.012 g, 0.03 mmol) obtained in Example 5 and 4-cyclopropylamino-thieno[3,2-d]pyrimidine-7-carboxylic acid (see WO 2011009687, 0.04 mmol) to obtain the title compound (10 mg, 57%).

Sources & evidence

ORD record
ord-946de24e371346c7b8f71c4e15bd4881
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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