1,1-Bis(methylthio)-2-nitroethylene → 1-[[(3S)-Hexahydro-3-[[2-nitro-1-[[4-(trifluoromethoxy)phenyl]amino]ethenyl]amino]-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine

HRID 1264636Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.CS[C:15](SC)=[CH:16][N+:17]([O-:19])=[O:18].[NH2:22][C@H:23]1[CH2:29][CH2:28][CH2:27][CH2:26][N:25]([CH2:30][C:31]([N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)=[O:32])[C:24]1=[O:38]>C(O)C>[N+:17]([CH:16]=[C:15]([NH:22][C@H:23]1[CH2:29][CH2:28][CH2:27][CH2:26][N:25]([CH2:30][C:31]([N:33]2[CH2:34][CH2:35][CH2:36][CH2:37]2)=[O:32])[C:24]1=[O:38])[NH:8][C:7]1[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-(trifluoromethoxy)aniline (20 mg, 0.11 mmol) and 1,1-bis(methylthio)-2-nitroethylene (19 mg, 0.12 mmol) in ethanol (0.25 mL) was heated at 80° C. for 5 h. To the mixture was added 1-[[(3S)-3-aminohexahydro-2-oxo-1H-azepin-1-yl]acetyl]pyrrolidine (27 mg, 0.11 mmol). The resulting solution was stirred at 80° C. for 14 h, and the mixture was then concentrated in vacuo. The residue was purified by preparative HPLC (YMC-PACK ODSA S5 (30×250 mm); flow rate 25 mL/min; gradient time 55 min) to furnish the title compound as a white solid (30 mg, 55%): MS (ESI, pos. ion spectrum) m/z 486; HPLC (method A) tR 3.59 min.

Workup

concentrationthe mixture was then concentrated in vacuo
customThe residue was purified by preparative HPLC (YMC-PACK ODSA S5 (30×250 mm); flow rate 25 mL/min; gradient time 55 min)

Sources & evidence

ORD record: ord-1da8cf4a7ae64a25ac1363317cc36e03
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06544981B2

Reaction notes

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