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

HRID 1264630Notes

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[CH:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17].C(N(CC)CC)C.[NH2:27][CH:28]1[CH2:34][CH2:33][C:32]2[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=2[N:30]([CH2:39][C:40]([N:42]2[CH2:46][CH2:45][CH2:44][CH2:43]2)=[O:41])[C:29]1=[O:47]>C(O)C>[C:16]([C:15]([C:18]#[N:19])=[C:14]([NH:27][CH:28]1[CH2:34][CH2:33][C:32]2[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=2[N:30]([CH2:39][C:40]([N:42]2[CH2:43][CH2:44][CH2:45][CH2:46]2)=[O:41])[C:29]1=[O:47])[NH:11][C:8]1[CH:9]=[CH:10][C:4]2[O:3][C:2]([CH3:1])=[CH:6][C:5]=2[CH:7]=1)#[N:17]

Participants

Conditions

Temperature: 80 °C

Procedure

Preparation of title compound. A solution of 2-methyl-5-benzofuranamine (0.24 mmol), 1,1-bis(methylthio-2,2-dicyanoethylene (34 mg, 0.20 mmol) and triethylamine (0.035 mL, 0.25 mmol) in ethanol (0.35 mL) was stirred at 80° C. for 4 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, 5% methanol/ethyl acetate) to afford the title compound (3 mg, 3% yield): MS (ESI, pos. ion spectrum) m/z 509; HPLC (method A) tR 3.80 min.

Workup

customthe resulting reaction
customThe reaction mixture was purified by column chromatography (silica, 5% methanol/ethyl acetate)

Sources & evidence

ORD record: ord-0ae0cd8413b64588ae4897cb0b3a898c
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544981B2

Reaction notes

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