Dimethyl Sulfoxide → HCID 86693782, compound

HRID 245072Notes

Reaction equation

C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[C:19]([CH3:20])=[C:18]([NH:21][C@@H:22]2[CH2:27][CH2:26][O:25][CH2:24][C@H:23]2[OH:28])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15].C(N(CC)CC)C>ClCCl.CCOC(C)=O>[Cl:11][C:12]1[C:19]([CH3:20])=[C:18]([NH:21][CH:22]2[CH2:27][CH2:26][O:25][CH2:24][C:23]2=[O:28])[CH:17]=[CH:16][C:13]=1[C:14]#[N:15]

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of oxalyl chloride (1.22 mL, 14.1 mmol) in dichloromethane (15 mL) at −60° C. is added dropwise a solution of dimethyl sulfoxide (2.08 mL, 29.3 mmol) in dichloromethane (15 mL) and stirred at −60° C. for 15 min. trans-2-chloro-4-[(3-hydroxytetrahydropyran-4-yl)amino]-3-methyl-benzonitrile (3.13 g, 11.7 mmol, Example 9) in dichloromethane (30 mL) is added to the solution and stirred at −60° C. for 30 min. Triethylamine (9 mL, 64.5 mmol) is added and the mixture is warmed to room temperature and stirred for 3 h. The mixture is diluted with EtOAc and washed twice with 1 N hydrochloric acid. The organic portion is dried over sodium sulfate, filtered, and concentrated in vacuo to give the crude title compound as an orange semi-solid (2.53 g, 81%). LC-ES/MS m/z 265.2 (M+1).

Workup

additionis added to the solution
temperaturethe mixture is warmed to room temperature
stirringstirred for 3 h
washwashed twice with 1 N hydrochloric acid
dry with materialThe organic portion is dried over sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-f28878f59fe64ba4ba41077a8d3a3513
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08658693B2

Reaction notes

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