Hydrazine hydrate (1:1) → HCID 178514346, compound

HRID 1664926Notes

Reaction equation

HRID 1664926 reaction equation
O.[NH2:2][NH2:3].[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:12]1[CH2:18][NH:17][C:16](=S)[C@H:15]([NH:20][C:21]([N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[C:37]4[C:32](=[N:33][CH:34]=[CH:35][CH:36]=4)[NH:31][C:30]3=[O:38])[CH2:25][CH2:24]2)=[O:22])[CH2:14][CH2:13]1>CO>[F:4][C:5]1[C:10]([F:11])=[CH:9][CH:8]=[CH:7][C:6]=1[C@H:12]1[CH2:18][NH:17][C:16](=[N:2][NH2:3])[C@H:15]([NH:20][C:21]([N:23]2[CH2:28][CH2:27][CH:26]([N:29]3[C:37]4[C:32](=[N:33][CH:34]=[CH:35][CH:36]=4)[NH:31][C:30]3=[O:38])[CH2:25][CH2:24]2)=[O:22])[CH2:14][CH2:13]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59340967N-[(3R,6S)-6-(2,3-Difluorophenyl)-2-thioxoazepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide

Product 1

HCID 178514346HCID 178514346, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine monohydrate (1.46 mL, 30.1 mmol) was added to a solution of N-[(3R,6S)-6-(2,3-difluorophenyl)-2-thioxoazepan-3-yl]-4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxamide (502 mg, 1.00 mmol) in methanol (20 mL). After 30 min, the reaction was concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated to give the title compound (515 mg). MS 499.1 (M+1).

Workup

  1. concentrationthe reaction was concentrated
  2. additionSaturated aqueous sodium bicarbonate was added
  3. extractionthe mixture was extracted with dichloromethane (3×)
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-cb8f90d21b754b5d86cbba8ea6335891
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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