N1-(4-chlorophenyl)-6-methylisoquinoline-1,5-diamine → N-(1-((4-chlorophenyl)amino)-6-methylisoquinolin-5-yl)-4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamide

HRID 1750865Notes

Reaction equation

HRID 1750865 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[CH:17]=[CH:16][C:15]([CH3:19])=[C:14]([NH2:20])[C:13]=3[CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1.[CH:21]1([NH:24][C:25]2[C:26]3[S:33][CH:32]=[C:31]([C:34](O)=[O:35])[C:27]=3[N:28]=[CH:29][N:30]=2)[CH2:23][CH2:22]1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:18]3[C:13](=[C:14]([NH:20][C:34]([C:31]4[C:27]5[N:28]=[CH:29][N:30]=[C:25]([NH:24][CH:21]6[CH2:22][CH2:23]6)[C:26]=5[S:33][CH:32]=4)=[O:35])[C:15]([CH3:19])=[CH:16][CH:17]=3)[CH:12]=[CH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 44478904N1-(4-chlorophenyl)-6-methylisoquinoline-1,5-diamineHCID 673596884-(Cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxylic acid

Product 1

HCID 71622580N-(1-((4-chlorophenyl)amino)-6-methylisoquinolin-5-yl)-4-(cyclopropylamino)thieno[3,2-d]pyrimidine-7-carboxamideYield 38.5%

Procedure

The procedures of <Step 3> of Example 1 were repeated, except for using N1-(4-chlorophenyl)-6-methylisoquinolin-1,5-diamine (0.04 g, 0.14 mmol) and 4-cyclopropylamino-thieno[3,2-d]pyrimidine-7-carboxylic acid (see WO 2011009687, 0.18 mmol) obtained in <Step 2> of Example 1 to obtain the title compound (27 mg, 38%).

Workup

  1. customobtained in <Step 2> of Example 1

Sources & evidence

ORD record
ord-630b6cee7c29420cb4bd9aac54c4ce67
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

Loading…