Hydrazine hydrate (1:1) → HCID 178440966, compound

HRID 1879626Notes

Reaction equation

[Cl:1][C:2]1[C:3](F)=[C:4]([C:12](=O)[CH:13]([CH:21]([C:25]2[CH:42]=[CH:41][C:28]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])=[O:30])=[CH:27][CH:26]=2)[CH2:22][CH2:23][CH3:24])[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.O.[NH2:46][NH2:47]>N1C=CC=CC=1.Cl>[Cl:20][C:17]1[CH:16]=[CH:15][C:14]([CH:13]([C:12]2[C:4]3[C:3](=[C:2]([Cl:1])[CH:7]=[C:6]([C:8]([F:9])([F:11])[F:10])[CH:5]=3)[NH:47][N:46]=2)[CH:21]([C:25]2[CH:26]=[CH:27][C:28]([C:29]([NH:31][CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])=[O:30])=[CH:41][CH:42]=2)[CH2:22][CH2:23][CH3:24])=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of the minor diastereomer of tert-butyl N-(4-{1-[2-[3-chloro-2-fluoro-5-(trifluoromethyl)phenyl]-1-(4-chlorophenyl)-2-oxoethyl]butyl}benzoyl)-β-alaninate (EXAMPLE 2, Step A, 71 mg, 0.108 mmol) in pyridine (5 mL) was added hydrazine hydrate (0.053 mL, 1.1 mmol). The mixture was stirred at 80° C. for one hour in a sealed tube. The mixture was diluted with 1 N HCl (aq), then extracted twice with EtOAc. The combined organic layers were dried over sodium sulfate, filtered, then concentrated to afford the title compound. This material was used directly in the next step without further purification. LC2 1.57 min. (M-tBu+H)+ 592.

Workup

extractionextracted twice with EtOAc
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-4fc824e7dfb04249a775229aa2a72ec2
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318667B2

Reaction notes

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