Ammonium Hydroxide → HCID 57633117, compound

HRID 2108760Notes

Reaction equation

HRID 2108760 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[N:18]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1)([O-])=O.[NH4+].[OH-]>CN(C=O)C.CO.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][C:11]([NH:13][C:14]2[S:15][CH:16]=[C:17]([C:19]3[C:27]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:21][CH:20]=3)[N:18]=2)=[O:12])[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 57633126HCID 57633126, compound

Product 1

HCID 57633117HCID 57633117, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Conditions

Temperature
100 °C

Procedure

2-(3-Nitro-phenyl)-N-[4-(1H-pyrrolo[2,3-b]pyridin-3-yl)-thiazol-2-yl]-acetamide (200 mg, 0.5 mmol) was taken in DMF-MeOH (5 mL) and added to sat. NH4OH (5 ml) and Fe powder (3eq, 83 mg). Then the suspension was heated overnight at 100° C. The brown colored reaction mixture was passed through a celite plug and washed with ethyl acetate. Then the reaction mixture was concentrated to dryness and taken up in ethyl acetate and extracted with water. The organic layer was dried and concentrated to give the desired product as a tan solid (50 mg, 30% yield).

Workup

  1. washwashed with ethyl acetate
  2. concentrationThen the reaction mixture was concentrated to dryness
  3. extractionextracted with water
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-3cbb334fdf9d437a967288278ae217a2
Source dataset
uspto-grants-2009_04
Patent number
US07514448B2

Reaction notes

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