Pyridine → HCID 178438565, compound

HRID 2048301Notes

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-c6bd729b685d46768bddb7e65262c50e
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592431B2

Reaction notes

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