4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide → HCID 178487939, compound
Reaction equation
Cl.Br[C:3]1[N:4]=[C:5]([C@H:13]2[CH2:18][CH2:17][C@H:16]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[CH2:15][CH2:14]2)[N:6]2[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[C:7]=12.[CH3:25][O:26][C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[CH:29]=[C:30]([C:37]([NH:39][C:40]1[CH:45]=[CH:44][C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][C:41]=1[O:55][CH3:56])=[O:38])[N:31]2[CH3:36]>>[CH3:25][O:26][C:27]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:28]=1[CH:29]=[C:30]([C:37]([NH:39][C:40]1[CH:45]=[CH:44][C:43]([C:3]3[N:4]=[C:5]([C@H:13]4[CH2:18][CH2:17][C@H:16]([N:19]5[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]5)[CH2:15][CH2:14]4)[N:6]4[CH:11]=[CH:10][N:9]=[C:8]([CH3:12])[C:7]=34)=[CH:42][C:41]=1[O:55][CH3:56])=[O:38])[N:31]2[CH3:36]Participants
3
Procedure
Reaction of 1-bromo-8-methyl-3-((trans)-4-(piperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine hydrochloride (40 mg) and 4-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (42 mg) according to the procedure described in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol) gave 4-methoxy-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(piperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-indole-2-carboxamide (8 mg).
Workup
- customdescribed in example 4 step 4c and purification by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol)
Sources & evidence
- ORD record
- ord-af41702dc015433fb5f668f3b9d51493
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658794B2
Reaction notes
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