5-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide → HCID 178486628, compound

HRID 245776Notes

Reaction equation

HRID 245776 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18](B4OC(C)(C)C(C)(C)O4)=[CH:17][C:16]=3[O:30][CH3:31])=[O:13])[N:9]([CH3:32])[C:6]2=[CH:7][N:8]=1.Br[C:34]1[N:35]=[C:36]([C@H:44]2[CH2:49][CH2:48][C@H:47]([N:50]3[CH2:55][CH2:54][N:53]([CH3:56])[CH2:52][CH2:51]3)[CH2:46][CH2:45]2)[N:37]2[CH:42]=[CH:41][N:40]=[C:39]([CH3:43])[C:38]=12>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][C:18]([C:34]4[N:35]=[C:36]([C@H:44]5[CH2:45][CH2:46][C@H:47]([N:50]6[CH2:51][CH2:52][N:53]([CH3:56])[CH2:54][CH2:55]6)[CH2:48][CH2:49]5)[N:37]5[CH:42]=[CH:41][N:40]=[C:39]([CH3:43])[C:38]=45)=[CH:17][C:16]=3[O:30][CH3:31])=[O:13])[N:9]([CH3:32])[C:6]2=[CH:7][N:8]=1

Participants

3

Reactant 2

HCID 673637125-methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamideHCID 178432912HCID 178432912, compound

Product 1

HCID 178486628HCID 178486628, compoundYield 60.6%

Procedure

5-Methoxy-N-(2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-methyl-1H-pyrrolo[2,3-c]pyridine-2-carboxamide (22 mg) and 1-bromo-8-methyl-3-((trans)-4-(4-methylpiperazin-1-yl)cyclohexyl)imidazo[1,5-a]pyrazine (20 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) to give 5-methoxy-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-c]pyridine-2-carboxamide (19 mg).

Workup

  1. custompurified by column chromatography (silica gel; dichloromethane with gradient 0 to 20% of methanol)

Sources & evidence

ORD record
ord-1662b9343e864f5e9e3d59a899135094
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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