N-methyl-2-pyrrolidone → HCID 90015288, compound

HRID 1057057Notes

Reaction equation

HRID 1057057 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)[CH:5]=[C:4]([Cl:19])[N:3]=1.Cl.[F:21][C:22]1([F:27])[CH2:26][CH2:25][NH:24][CH2:23]1.CN1C(=O)CCC1.CCN(C(C)C)C(C)C>>[Cl:19][C:4]1[CH:5]=[C:6]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)[CH:7]=[C:2]([N:24]2[CH2:25][CH2:26][C:22]([F:27])([F:21])[CH2:23]2)[N:3]=1

Participants

5

Reactant 4

HCID 13387N-methyl-2-pyrrolidoneHCID 81531DiisopropylethylamineHCID 249034823,3-Difluoropyrrolidine hydrochlorideHCID 90015386HCID 90015386, compound

Product 1

HCID 90015288HCID 90015288, compound

Conditions

Temperature
140 °C

Procedure

To a suspension of tert-butyl 3-(2,6-dichloro-4-pyridyl)azetidine-1-carboxylate (1-a, 472 mg, 1.557 mmol), 3,3-difluoropyrrolidine hydrochloride (1.12 g, 5.0 equiv., 7.784 mmol) in NMP (3.0 mL, 31 mmol) in a microwave vial was added DIPEA (1.90 mL, 7.0 equiv., 10.90 mmol)), and the reaction was maintained at 140° C. for 30 min and then at 150° C. for 30 min in the microwave machine. LCMS showed more than 95% conversion. The crude was used without further treatment. LCMS: m/z 374 (M+H).

Sources & evidence

ORD record
ord-a708db1eb52842cea8d81273d5bb4127
Source dataset
uspto-grants-2016_07
Patent number
US09399636B2

Reaction notes

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