Methanol → HCID 66738893, compound

HRID 1640697Notes

Reaction equation

Br[C:2]1[C:3](=[O:19])[N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:5]([CH3:8])=[CH:6][N:7]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH3:39][S:40]([C:43]1[CH:44]=[CH:45][C:46](N)=[N:47][CH:48]=1)(=[O:42])=[O:41].[CH2:50]([N:52]([CH2:55]C)CC)C.C[OH:58]>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:8][C:5]1[N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[CH:10]=2)[C:3](=[O:19])[C:2]([C:50]([NH:52][CH2:55][C:46]2[CH:45]=[CH:44][C:43]([S:40]([CH3:39])(=[O:42])=[O:41])=[CH:48][N:47]=2)=[O:58])=[N:7][CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A high-pressure steel reactor (Parr) with CO-gas inlet was charged with 3-bromo-6-methyl-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one (SM1, 0.30 g, 0.89 mmol), Pd(OAc)2 (0.035 g, 0.16 mmol), PPh3 (0.070 g, 0.26 mmol) and 5-methanesulfonyl-pyridine-2-ylamine (0.46 g, 1.79 mmol) in methanol (25 ml). To this mixture was added triethylamine (1.5 ml, 1.09 g, 10 mmol) and a magnetic stirrer bar. The reactor was ventilated with CO and 6 atmospheres CO-pressure was applied to the system. The reactor was heated to 90° C., the mixture was vigorously stirred, and the reaction was allowed to proceed for 4 h, and was then allowed to cool. The volatiles were removed in vacuo and the crude product was purified by preparative HPLC, which gave 0.22 g (53%) of 5-methyl-N-{[5-(methylsulfonyl)-pyridin-2-yl]methyl}-3-oxo-4-[3-(trifluoromethyl)-phenyl]-3,4-dihydropyrazine-2-carboxamide as a white solid, after freeze-drying the pure fractions.

Workup

temperatureto cool
customThe volatiles were removed in vacuo
customthe crude product was purified by preparative HPLC, which

Sources & evidence

ORD record: ord-ade09c7640d34a5581492ffd4d6b5bde
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08114881B2

Reaction notes

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