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 178487937, compound

HRID 245751Notes

Reaction equation

HRID 245751 reaction equation
Br[C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([CH2:18][N:19]([CH3:21])[CH3:20])[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][CH:30]=[C:29]2[C:25]=1[CH:26]=[C:27]([C:34]([NH:36][C:37]1[CH:42]=[CH:41][C:40](B3OC(C)(C)C(C)(C)O3)=[CH:39][C:38]=1[O:52][CH3:53])=[O:35])[N:28]2[CH3:33]>>[CH3:20][N:19]([CH2:18][C@H:15]1[CH2:16][CH2:17][C@H:12]([C:4]2[N:5]3[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]3=[C:2]([C:40]3[CH:41]=[CH:42][C:37]([NH:36][C:34]([C:27]4[N:28]([CH3:33])[C:29]5[C:25]([CH:26]=4)=[C:24]([O:23][CH3:22])[CH:32]=[CH:31][CH:30]=5)=[O:35])=[C:38]([O:52][CH3:53])[CH:39]=3)[N:3]=2)[CH2:13][CH2:14]1)[CH3:21]

Participants

3

Reactant 2

HCID 673656514-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-indole-2-carboxamideHCID 178432908HCID 178432908, compound

Product 1

HCID 178487937HCID 178487937, compoundYield 28.2%

Procedure

1-((Trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)-N,N-dimethylmethanamine (26 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 (32 mg) were used according to the procedure described in example 4 step 4c and the crude product was purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid). Proper fractions were collected and made basic with aqueous sodium hydrogencarbonate, extracted with dichloromethane, organic layer dried (Na2SO4) and concentrated in vacuo to give N-(4-(3-((trans)-4-((dimethylamino)methyl)cyclohexyl)-8-methylimidazo[1,5-a]pyrazin-1-yl)-2-methoxyphenyl)-4-methoxy-1-methyl-1H-indole-2-carboxamide (12 mg).

Workup

  1. customthe crude product was purified by prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid)
  2. customProper fractions were collected
  3. extractionextracted with dichloromethane, organic layer
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a6694340e7f94fcba4e2eebbf5be200d
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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