2-Cyano-3,3-bis(methylthio)acrylamide → 2-Cyano-3-[[(3S)-hexahydro-2-oxo-1-(phenylmethyl)-1H-azepin-3-yl]amino]-3-[(2-methyl-5-benzofuranyl)amino]-propenamide

HRID 1264632Notes

Reaction equation

HRID 1264632 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)=[C:15]([C:19]#[N:20])[C:16]([NH2:18])=[O:17].[NH2:23][CH:24]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:25]1=[O:38]>C(O)C>[C:19]([C:15](=[C:14]([NH:23][C@H:24]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:25]1=[O:38])[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)[C:16]([NH2:18])=[O:17])#[N:20]

Participants

5

Reactant 3

HCID 27477462-Cyano-3,3-bis(methylthio)acrylamideHCID 31574842-Methyl-5-benzofuranamineHCID 186125993-Amino-1-benzyl-azepan-2-one

Product 1

HCID 700320362-Cyano-3-[[(3S)-hexahydro-2-oxo-1-(phenylmethyl)-1H-azepin-3-yl]amino]-3-[(2-methyl-5-benzofuranyl)amino]-propenamideYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Preparation of title compound. A solution of 2-methyl-5-benzofuranamine (32 mg, 0.22 mmol) and 3,3-bis(methylthio)-2-cyanoacrylamide (41 mg, 0.22 mmol) in ethanol (0.35 mL) was stirred at 80° C. After stirring for 5 h, a solution of 3-aminohexahydro-1-phenylmethyl-2H-azepin-2-one (74 mg, 0.29 mmol) in ethanol (0.74 mL) was added. After stirring at 80° C. for 2 days, the reaction was purified by column chromatography (silica, 1% methanol/dichloromethane) to afford the title compound (37 mg, 37% yield): MS (ESI, pos. ion spectrum) m/z 458; HPLC (method A) tR 4.13 min.

Workup

  1. stirringAfter stirring at 80° C. for 2 days
  2. customthe reaction was purified by column chromatography (silica, 1% methanol/dichloromethane)

Sources & evidence

ORD record
ord-44dae7d193bc481b8840d58d8d9c28f4
Source dataset
uspto-grants-2003_04
Patent number
US06544981B2

Reaction notes

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