Water → HCID 117987809, compound

HRID 2206099Notes

Reaction equation

HRID 2206099 reaction equation
[CH:1]1([N:6]2[C:14]3[C:13]([C:15]#[N:16])=[CH:12][N:11]=[C:10]([O:17][CH3:18])[C:9]=3[C:8]([C:19]3[CH:20]=[N:21][NH:22][CH:23]=3)=[CH:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:27][C:28]([NH2:30])=[O:29].O>C1COCC1>[C:15]([C:13]1[C:14]2[N:6]([CH:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:7]=[C:8]([C:19]3[CH:20]=[N:21][N:22]([CH2:27][C:28]([NH2:30])=[O:29])[CH:23]=3)[C:9]=2[C:10]([O:17][CH3:18])=[N:11][CH:12]=1)#[N:16]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 117987652HCID 117987652, compound

Product 1

HCID 117987809HCID 117987809, compoundYield 41.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-cyclopentyl-4-methoxy-3-(1H-pyrazol-4-yl)-1H-pyrrolo[3,2-c]pyridine-7-carbonitrile (55.3 mg) in THF (2 mL) was added sodium hydride (dispersion in mineral oil, 14.4 mg) at 0° C., and the mixture was stirred for 1 hr. To the reaction mixture was added 2-bromoacetamide (29.8 mg) at 0° C., and the reaction mixture was stirred overnight. The reaction mixture was poured into water, and the mixture was extracted twice with ethyl acetate and THF. The combined organic layers was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane/methanol) to give the title compound (27.5 mg).

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. extractionthe mixture was extracted twice with ethyl acetate and THF
  3. washThe combined organic layers was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane/methanol)

Sources & evidence

ORD record
ord-34ef4117c68f4bcdb88f3a3c409405d4
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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