4-Hydrazino-2-methylpyridine → 5-[(2S)-2-[[(1,1-Dimethylethyl)diphenylsilyl]oxy]propyl]-N-[4-fluoro-3-(trifluoromethyl)phenyl]-1-(2-methyl-4-pyridinyl)-1H-1,2,4-triazol-3-amine

HRID 1623567Notes

Reaction equation

CS[C:3](=[N:28][C:29]1[CH:34]=[CH:33][C:32]([F:35])=[C:31]([C:36]([F:39])([F:38])[F:37])[CH:30]=1)[NH:4][C:5](=O)[CH2:6][C@@H:7]([O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:8].[NH:40]([C:42]1[CH:47]=[CH:46][N:45]=[C:44]([CH3:48])[CH:43]=1)[NH2:41]>CN(C=O)C.[Hg](Cl)Cl>[CH3:24][C:23]([Si:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:9][C@@H:7]([CH3:8])[CH2:6][C:5]1[N:40]([C:42]2[CH:47]=[CH:46][N:45]=[C:44]([CH3:48])[CH:43]=2)[N:41]=[C:3]([NH:28][C:29]2[CH:34]=[CH:33][C:32]([F:35])=[C:31]([C:36]([F:38])([F:37])[F:39])[CH:30]=2)[N:4]=1)([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 80 °C

Procedure

Mercury(II) chloride (1.8 g, 6.5 mmol) was added to a stirred solution of intermediate D9 (prepared according to Description 9) (3.8 g, 6.5 mmol) and 4-hydrazino-2-methylpyridine (0.8 g, 6.5 mmol) in DMF (65 mL) at room temperature. The reaction mixture was heated at 80° C. for 140 min. The cooled reaction mixture was poured onto ice and the precipitated product was collected by filtration to give a yellow semi-solid. Yield: 4.2 g of intermediate D14 (101.2%).

Workup

customThe cooled reaction mixture
additionwas poured onto ice
filtrationthe precipitated product was collected by filtration
customto give a yellow semi-solid

Sources & evidence

ORD record: ord-6ee9d5b9079f4d2c8ff5a44df54d9a32
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778974B2

Reaction notes

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