Methylamine → HCID 25177442, compound

HRID 2088494Notes

Reaction equation

[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[N:11][C:10]([C:13]2[CH:17]=[C:16]([CH:18]=O)[S:15][C:14]=2[CH3:20])=[CH:9][N:8]=1)=[O:5].CC1C=CC(S([CH2:36][N:37]=[CH2:38])(=O)=O)=CC=1.[CH3:39][NH2:40]>CO>[F:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([F:25])[C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[N:11][C:10]([C:13]2[CH:17]=[C:16]([C:18]3[N:40]([CH3:39])[CH:36]=[N:37][CH:38]=3)[S:15][C:14]=2[CH3:20])=[CH:9][N:8]=1)=[O:5]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of 2,6-difluoro-N-(5-(5-formyl-2-methylthiophen-3-yl)pyrazin-2-yl)benzamide (A, 1.8 mmol) and p-tosylmethyl isocyanide (2 mmol) in methanol (18 mL) was added of a solution of methylamine (4 mmol, 2N in methanol). The mixture was heated in the microwave reactor at 110° C. for 2 h. Removal of solvent and purification of residue by flash chromatography gave 2,6-difluoro-N-(5-(2-methyl-5-(1-methyl-1H-imidazol-5-yl)thiophen-3-yl)pyrazin-2-yl)benzamide (B, 0.24 g) as yellowish solids. 1H-NMR (CD3OD) □9.50 (s, 1H), 8.69 (s, 1H), 7.70 (s, 1H), 7.5 (m, 2H), 7.1 (m, 3H), 3.71 (s, 3H), 2.72 (s, 3H)ppm; ESMS calcd for C20H15F2N5OS: 411.1. Found: 412.1 (M+H+).

Workup

customRemoval of solvent and purification of residue by flash chromatography

Sources & evidence

ORD record: ord-8312b199539c4f48ae606aad327cb7a0
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08435996B2

Reaction notes

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