Hydrazine → HCID 178461225, compound

HRID 81103Notes

Reaction equation

HRID 81103 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]([CH2:31][C@H:32]4[CH2:37][CH2:36][C@H:35]([CH3:38])[CH2:34][CH2:33]4)[C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][C@H:20]4[C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[N:18][C:14]=3[CH:13]=[C:12]([C:39]([O:41]C)=O)[N:11]=2)[CH:7]=[N:8][CH:9]=1>CO.ClCCl>[Cl:3][C:4]1[CH:5]=[C:6]([C:10]2[C:15]3[N:16]([CH2:31][C@H:32]4[CH2:33][CH2:34][C@H:35]([CH3:38])[CH2:36][CH2:37]4)[C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][C@H:20]4[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[N:18][C:14]=3[CH:13]=[C:12]([C:39]([NH:1][NH2:2])=[O:41])[N:11]=2)[CH:7]=[N:8][CH:9]=1

Participants

5

Reactant 2

HCID 9321HydrazineHCID 178496982HCID 178496982, compound

Product 1

HCID 178461225HCID 178461225, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Hydrazine (9.2 mL, 293 mmol) was added to methyl 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carboxylate (4.11 g, 7.33 mmol) dissolved in methanol (36.6 mL), and the solution was stirred at room temperature for 30 minutes. The mixture was diluted with dichloromethane and washed with water and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbohydrazide. MS ESI calc'd. for C30H34ClN7O2 [M+H]+ 560. found 560.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-004a895957434ff0ad2609c8220eddfd
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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