Hydrazine hydrate (1:1) → HCID 66990952, compound

HRID 2367238Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][NH:12][C:13]1[N:18]=[C:17]([N:19]2[C@H:24]([C:25]([F:28])([F:27])[F:26])[CH2:23][CH2:22][C@H:21]([C:29]([NH:31][CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[O:30])[CH2:20]2)[CH:16]=[C:15]([C:38]2[CH:43]=[CH:42][C:41]([C:44]#[N:45])=[C:40](F)[CH:39]=2)[N:14]=1.O.[NH2:48][NH2:49]>C(O)C>[NH2:45][C:44]1[C:41]2[C:40](=[CH:39][C:38]([C:15]3[N:14]=[C:13]([NH:12][CH2:11][C:4]4[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=4[O:2][CH3:1])[N:18]=[C:17]([N:19]4[C@H:24]([C:25]([F:28])([F:27])[F:26])[CH2:23][CH2:22][C@H:21]([C:29]([NH:31][CH:32]5[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]5)=[O:30])[CH2:20]4)[CH:16]=3)=[CH:43][CH:42]=2)[NH:49][N:48]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To cis-1-[2-({[2,4-bis(methyloxy)phenyl]methyl}amino)-6-(4-cyano-3-fluorophenyl)-4-pyrimidinyl]-N-cyclohexyl-6-(trifluoromethyl)-3-piperidinecarboxamide (304 mg, 0.48 mmol) in ethanol (6 mL) was added hydrazine monohydrate (0.47 mL, 9.5 mmol), and the reaction mixture was stirred overnight at 100° C. into a sealed tube. The reaction was allowed to cool to room temperature and poured onto water (˜200 mL). A white precipitate was formed. The mixture was filtered, and the solid was air dried for 2 hours to afford the title compound (270 mg) as a white solid. LC-MS (ES) m/z=653 [M+H]+.

Workup

temperatureto cool to room temperature
additionpoured onto water (˜200 mL)
customA white precipitate was formed
filtrationThe mixture was filtered
customdried for 2 hours

Sources & evidence

ORD record: ord-4ad30121e2e449c588f044b3328492c6
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08697685B2

Reaction notes

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