Pyridine → HCID 178438565, compound

HRID 519561Notes

Reaction equation

[C:1]([NH:4][NH:5][C:6]([C@H:8]1[CH2:13][CH2:12][C@H:11]([N:14]2[C:19](=[O:20])[C:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25](C4C=CC=CC=4C#N)=[CH:24][CH:23]=3)=[C:17]([CH2:36][CH2:37][CH3:38])[N:16]3[N:39]=[CH:40][N:41]=[C:15]23)[CH2:10][CH2:9]1)=[O:7])(=O)[CH3:2].[C:42]1([CH3:52])[CH:47]=[CH:46][C:45](S(Cl)(=O)=O)=[CH:44][CH:43]=1.[N:53]1C=CC=CC=1>C(OCC)(=O)C>[CH3:2][C:1]1[O:7][C:6]([C@H:8]2[CH2:13][CH2:12][C@H:11]([N:14]3[C:19](=[O:20])[C:18]([CH2:21][C:22]4[CH:23]=[CH:24][C:25]([C:43]5[C:42]([C:52]#[N:53])=[CH:47][CH:46]=[CH:45][CH:44]=5)=[CH:26][CH:27]=4)=[C:17]([CH2:36][CH2:37][CH3:38])[N:16]4[N:39]=[CH:40][N:41]=[C:15]34)[CH2:10][CH2:9]2)=[N:5][N:4]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of trans-N′-acetyl-4-{6-[(2′-cyanobiphenyl-4-yl)methyl]-5-oxo-7-propyl[1,2,4]triazolo[1,5-a]pyrimidin-4(5H)-yl}cyclohexanecarbohydrazide (0.4 g), p-toluenesulfonyl chloride (0.42 g) and pyridine (10 mL) was stirred at 110° C. for 5 hr. The reaction mixture was diluted with ethyl acetate, washed with 1 N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.33 g, 85%).

Workup

washwashed with 1 N hydrochloric acid
dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-6fb019d4bd7a4f758c0735e48f80ecc5
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115136B2

Reaction notes

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