Ammonium Chloride → HCID 68525354, compound

HRID 1437442Notes

Reaction equation

[Cl-].[NH4+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([C@@H:10]([NH:13][C:14]2[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[C:16]([NH:23][C:24]3[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=3)[N:15]=2)[CH2:11][OH:12])=[CH:6][CH:5]=1.C([O-])(=O)C.[NH4+]>CO.C1COCC1.[Zn]>[NH2:20][C:19]1[C:14]([NH:13][C@H:10]([C:7]2[CH:6]=[CH:5][C:4]([F:3])=[CH:9][CH:8]=2)[CH2:11][OH:12])=[N:15][C:16]([NH:23][C:24]2[CH:28]=[C:27]([CH3:29])[NH:26][N:25]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of saturated ammonium chloride (3 ml) was added slowly to a suspension of (R)-2-(4-fluorophenyl)-2-(6-(5-methyl-1H-pyrazol-3-ylamino)-3-nitropyridin-2-ylamino)ethanol (Method 63, 0.29 g, 0.78 mmol) and zinc dust (0.25 g, 3.9 mmol) in a mixture of MeOH-THF (1:1, 20 ml). The mixture was stirred at 25° C. for 1 hour. Saturated ammonium acetate solution (5 ml) was added and the mixture was stirred for another 30 minutes. The Zn dust was removed by filtration and the cake was washed with EtOAc (20 ml). The organic layer was separated, washed with brine (10 ml) and dried over sodium sulfate. After removal of solvent, the title compound was obtained which was used directly for the next step without purification. MS: Calcd.: 342. Found: [M+H]+ 343.

Workup

stirringthe mixture was stirred for another 30 minutes
customThe Zn dust was removed by filtration
washthe cake was washed with EtOAc (20 ml)
customThe organic layer was separated
washwashed with brine (10 ml)
dry with materialdried over sodium sulfate
customAfter removal of solvent

Sources & evidence

ORD record: ord-d737e20daf294b8c8df124e4eae140b9
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622482B2

Reaction notes

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