Dimethylformamide → HCID 86641104, compound

HRID 1809610Notes

Reaction equation

Br[C:2]1[CH:41]=[CH:40][C:5]([O:6][C:7]2[CH:8]=[C:9]([S:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[Cl:39])[C:10]([NH:13][C:14]3[S:18][N:17]=[C:16]([CH:19]4[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]4)[N:15]=3)=[N:11][CH:12]=2)=[CH:4][CH:3]=1.C[Li].C([Li])CCC.CN(C)[CH:51]=[O:52].[NH4+].[Cl-]>C1COCC1>[Cl:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[S:32][C:9]1[C:10]([NH:13][C:14]2[S:18][N:17]=[C:16]([CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)[N:15]=2)=[N:11][CH:12]=[C:7]([O:6][C:5]2[CH:40]=[CH:41][C:2]([CH:51]=[O:52])=[CH:3][CH:4]=2)[CH:8]=1

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl 4-(5-(5-(4-bromophenoxy)-3-(2-chlorophenylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (500 mg, 0.741 mmol) was dissolved in THF (7 mL) and cooled to −78° C. Methyllithium (556 μL, 0.889 mmol) was added and the reaction was stirred for 5 minutes. Butyllithium (356 μL, 0.889 mmol) was added and the reaction was stirred for 5 minutes. N,N-dimethylformamide (115 μL, 1.48 mmol) was added and the reaction was slowly warmed to ambient temperature. The reaction was poured into NH4Cl, extracted with EtOAc, concentrated and purified on silica gel (5 to 10% EtOAc in hexanes) to afford tert-butyl 4-(5-(3-(2-chlorophenylthio)-5-(4-formylphenoxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)piperidine-1-carboxylate (183 mg, 0.293 mmol, 39.6% yield) as a white solid.

Workup

stirringthe reaction was stirred for 5 minutes
temperaturethe reaction was slowly warmed to ambient temperature
extractionextracted with EtOAc
concentrationconcentrated
custompurified on silica gel (5 to 10% EtOAc in hexanes)

Sources & evidence

ORD record: ord-f969e468a301459b8f9d7fd12e0a1d52
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08362037B2

Reaction notes

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