HCID 67364747, compound → HCID 178487941, compound

HRID 245758Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17](B4OC(C)(C)C(C)(C)O4)=[CH:16][C:15]=3[O:29][CH3:30])=[O:12])[N:8]([CH3:31])[C:5]2=[N:6][CH:7]=1.Br[C:33]1[N:34]=[C:35]([C@H:43]2[CH2:48][CH2:47][C@H:46]([N:49]3[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]3)[CH2:45][CH2:44]2)[N:36]2[CH:41]=[CH:40][N:39]=[C:38]([CH3:42])[C:37]=12>>[Cl:1][C:2]1[CH:3]=[C:4]2[CH:10]=[C:9]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([C:33]4[N:34]=[C:35]([C@H:43]5[CH2:44][CH2:45][C@H:46]([N:49]6[CH2:50][CH2:51][N:52]([CH3:55])[CH2:53][CH2:54]6)[CH2:47][CH2:48]5)[N:36]5[CH:41]=[CH:40][N:39]=[C:38]([CH3:42])[C:37]=45)=[CH:16][C:15]=3[O:29][CH3:30])=[O:12])[N:8]([CH3:31])[C:5]2=[N:6][CH:7]=1

Participants

Reactant 2

HCID 67364747HCID 67364747, compound

HCID 178432912HCID 178432912, compound

Product 1

HCID 178487941HCID 178487941, compoundYield 56.3%

Procedure

5-Chloro-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (34 mg) and 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (30 mg) were reacted according to the procedure described in example 4 step 4c and purified by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol (containing 0.1% ammonium hydroxide)) to give 5-chloro-N-(2-methoxy-4-(8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazin-1-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridine-2-carboxamide (27 mg).

Workup

custompurified by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol (containing 0.1% ammonium hydroxide))

Sources & evidence

ORD record: ord-f095b99fa3f2402689714f16863d7105
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658794B2

Reaction notes

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