Ammonium Chloride → HCID 11224101, compound

HRID 1358485Notes

Reaction equation

HRID 1358485 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([N:25]1[CH:29]=[C:28]([C:30]([NH2:32])=[O:31])[N:27]=[CH:26]1)[CH2:11][CH2:12][N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([N+:22]([O-])=O)[CH:20]=2)[CH:15]=[CH:14]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:22][C:19]1[CH:20]=[C:21]2[C:16]([CH:15]=[CH:14][N:13]2[CH2:12][CH2:11][C@@H:10]([N:25]2[CH:29]=[C:28]([C:30]([NH2:32])=[O:31])[N:27]=[CH:26]2)[CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[CH:17][CH:18]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 11271068HCID 11271068, compound

Product 1

HCID 11224101HCID 11224101, compoundYield 94.7%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a mechanically stirred mixture of 1-[(R)-1-(tert-butyldimethylsilyloxy)-4-(6-nitroindol-1-yl)-2-butyl]imidazole-4-carboxamide (450 mg, 0.98 mmol) and ammonium chloride (45 mg) in ethanol (10 ml) and water (5 ml) was added portionwise iron powder (450 mg) at 90° C. The resulting mixture was stirred for 40 minutes at 90° C. After cooling, the insoluble material was filtered through Celite and washed with ethanol and ethyl acetate. The filtrate and the washing were combined and concentrated in vacuo. The resulting residue was extracted with ethyl acetate and washed with brine. The organic layer was dried (sodium sulfate) and concentrated in vacuo to give 1-[(R)-4-(6-aminoindol-1-yl)-1-(tert-butyldimethylsilyloxy)-2-butyl]imidazole-4-carboxamide (397 mg, 94.7%). This material was used for the next reaction without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe insoluble material was filtered through Celite
  3. washwashed with ethanol and ethyl acetate
  4. concentrationconcentrated in vacuo
  5. extractionThe resulting residue was extracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialThe organic layer was dried (sodium sulfate)
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5691278a1c654c7ba3682b083781f9c8
Source dataset
uspto-grants-2003_07
Patent number
US06596738B1

Reaction notes

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