Triethylamine → 1-[[2,3,4,5-Tetrahydro-3-[[1-[(2-methyl-5-benzofuranyl)amino]-2-nitroethenyl]amino]-2-oxo-1H-1-benzazepin-1-yl]acetyl]pyrrolidine

HRID 1264631Notes

Reaction equation

[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][C:5]=2[CH:6]=1.CS[C:14](SC)=[CH:15][N+:16]([O-:18])=[O:17].C(N(CC)CC)C.[NH2:28][CH:29]1[CH2:35][CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=2[N:31]([CH2:40][C:41]([N:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)=[O:42])[C:30]1=[O:48]>C(O)C>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([NH:11][C:14]([NH:28][CH:29]3[CH2:35][CH2:34][C:33]4[CH:36]=[CH:37][CH:38]=[CH:39][C:32]=4[N:31]([CH2:40][C:41]([N:43]4[CH2:44][CH2:45][CH2:46][CH2:47]4)=[O:42])[C:30]3=[O:48])=[CH:15][N+:16]([O-:18])=[O:17])=[CH:7][C:5]=2[CH:6]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 2-methyl-5-benzofuranamine (0.24 mmol), 1,1-bis(methylthio)-2-nitroethylene (40 mg, 0.24 mmol) and triethylamine (0.035 mL, 0.25 mmol) in ethanol (0.35 mL) was stirred at 80° C. for 2 h. To the mixture was added 1-[(3-amino-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-1-yl)acetyl]pyrrolidine (70 mg, 0.24 mmol) and the resulting reaction was stirred at 80° C. overnight. The reaction mixture was purified by column chromatography (silica, 3% methanol/ethyl acetate) to provide the title compound (29 mg, 24% yield): MS (ESI, pos. ion spectrum) m/z 504; HPLC (method A) tR 3.67 min.

Workup

customthe resulting reaction
customThe reaction mixture was purified by column chromatography (silica, 3% methanol/ethyl acetate)

Sources & evidence

ORD record: ord-050b87056bde4874a785b99d82e7810e
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544981B2

Reaction notes

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