Methanesulfonic Acid → HCID 90311943, compound

HRID 1505825Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([NH:12][C:13]([C:15]2[C:16](=[O:33])[C:17]([O:31][CH3:32])=[C:18]([C:27]([O:29][CH3:30])=[O:28])[N:19]([CH2:21][CH:22]([O:25]C)[O:23]C)[CH:20]=2)=[O:14])[CH2:11][CH2:10]1.CS(O)(=O)=O>C(#N)C.C(O)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([NH:12][C:13]([C:15]2[C:16](=[O:33])[C:17]([O:31][CH3:32])=[C:18]([C:27]([O:29][CH3:30])=[O:28])[N:19]([CH2:21][CH:22]([OH:23])[OH:25])[CH:20]=2)=[O:14])[CH2:10][CH2:11]1

Participants

Conditions

Temperature: 70 °C

Procedure

Methyl 5-(1-(2,4-difluorophenyl)cyclopropylcarbamoyl)-1-(2,2-dimethoxyethyl)-3-methoxy-4-oxo-1,4-dihydropyridine-2-carboxylate (27-1B, 0.150 g, 0.32 mmol) in acetonitrile (1.5 mL) and acetic acid (0.2 mL) was treated with methanesulfonic acid (0.05 mL), sealed with a yellow cap, and heated to 70° C. After 16 hours, the mixture was cooled to afford a crude solution of methyl 5-(1-(2,4-difluorophenyl)cyclopropylcarbamoyl)-1-(2,2-dihydroxyethyl)-3-methoxy-4-oxo-1,4-dihydropyridine-2-carboxylate 27-C. LCMS-ESI+ (m/z): [M+H]+ calculated for C18H19F2N2O7: 439; found: 439.

Workup

customsealed with a yellow cap
temperaturethe mixture was cooled

Sources & evidence

ORD record: ord-6144e4885d7041848aa324e0dce11bb2
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216996B2

Reaction notes

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