Dimethylformamide → HCID 68153712, compound

HRID 1405358Notes

Reaction equation

O=[C:2]=[N:3]S(Cl)(=O)=O.[C:8]12([CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)[N:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH2:12][CH2:11][N:10]1[CH:19]=[CH:20][CH:21]=[C:9]21.CN(C)C=O>C1COCC1>[C:2]([C:19]1[N:10]2[CH2:11][CH2:12][N:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:8]3([CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])[CH2:23][CH2:22]3)[C:9]2=[CH:21][CH:20]=1)#[N:3]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of N-(oxomethylene)sulfamoyl chloride (23.9 μL, 0.27 mmol) in THF (200.0 μL) was slowly added to a solution of 1-tert-butyl 2′-ethyl 3′,4′-dihydro-2′H-spiro[piperidine-4,1′-pyrrolo[1,2-a]pyrazine]-1,2′-dicarboxylate (100 mg, 0.27 mmol) in THF (1.0 mL) at −78° C. under nitrogen. The reaction mixture was stirred for 1 hour at −78° C. N,N-dimethylformamide (39.9 μL, 0.51 mmol) was then slowly added to the cold reaction mixture. The reaction mixture was then allowed to slowly warm to room temperature. The reaction was filtered and purified by reverse phase preparatory-LC-MS (10-99% CH3CN/H2O) using HCl modifier to give 1-tert-butyl 2′-ethyl 6′-cyano-3′,4′-dihydro-2′H-spiro[piperidine-4,1′-pyrrolo[1,2-a]pyrazine]-1,2′-dicarboxylate. ESI-MS m/z calc. 388.2, found 389.3 (M+1)+; Retention time: 1.82 minutes (3 minute run).

Workup

temperatureto slowly warm to room temperature
filtrationThe reaction was filtered
custompurified by reverse phase preparatory-LC-MS (10-99% CH3CN/H2O)

Sources & evidence

ORD record: ord-9847bfd6f5114416b9750c49b1c9a063
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916565B2

Reaction notes

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