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 178487947, compound

HRID 245662Notes

Reaction equation

Br[C:2]1[N:3]=[C:4]([C@H:12]2[CH2:17][CH2:16][C@H:15]([N:18]3[CH2:23][CH2:22][N:21]([C:24](=[O:26])[CH3:25])[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)[N:5]2[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]=12.[CH3:27][O:28][C:29]1[CH:37]=[CH:36][CH:35]=[C:34]2[C:30]=1[CH:31]=[C:32]([C:39]([NH:41][C:42]1[CH:47]=[CH:46][C:45](B3OC(C)(C)C(C)(C)O3)=[CH:44][C:43]=1[O:57][CH3:58])=[O:40])[N:33]2[CH3:38]>>[C:24]([N:21]1[CH2:22][CH2:23][N:18]([C@H:15]2[CH2:16][CH2:17][C@H:12]([C:4]3[N:5]4[CH:10]=[CH:9][N:8]=[C:7]([CH3:11])[C:6]4=[C:2]([C:45]4[CH:46]=[CH:47][C:42]([NH:41][C:39]([C:32]5[N:33]([CH3:38])[C:34]6[C:30]([CH:31]=5)=[C:29]([O:28][CH3:27])[CH:37]=[CH:36][CH:35]=6)=[O:40])=[C:43]([O:57][CH3:58])[CH:44]=4)[N:3]=3)[CH2:13][CH2:14]2)[CH2:19][CH2:20]1)(=[O:26])[CH3:25]

Participants

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-carboxamide

HCID 178473908HCID 178473908, compound

Product 1

HCID 178487947HCID 178487947, compound

Procedure

Using the procedure described in example 1 step 1f 1-(4-((trans)-4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)cyclohexyl)piperazin-1-yl)ethanone (0.059 mmol, 25 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 (0.059 mmol, 26 mg) gave after purification on prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid) 11 mg of the title compound.

Workup

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customafter purification on prep-HPLC (column Luna C18(2); gradient acetonitrile/water with constant 0.003M trifluoroacetic acid) 11 mg of the title compound

Sources & evidence

ORD record: ord-94b385af2841461a9564b0769b4f2248
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658794B2

Reaction notes

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