Cyclopentanemethylamine → 4-[(Cyclopentylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

HRID 2217938노트

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HRID 2217938 반응식
F[C:2]1[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:14][C:15]([F:18])([F:17])[F:16])[CH2:9][C:10]([F:13])([F:12])[F:11])=[O:7])=[CH:4][C:3]=1[N+:21]([O-:23])=[O:22].[CH:24]1([CH2:29][NH2:30])[CH2:28][CH2:27][CH2:26][CH2:25]1>CCO>[CH:24]1([CH2:29][NH:30][C:2]2[CH:20]=[CH:19][C:5]([C:6]([N:8]([CH2:9][C:10]([F:12])([F:13])[F:11])[CH2:14][C:15]([F:17])([F:18])[F:16])=[O:7])=[CH:4][C:3]=2[N+:21]([O-:23])=[O:22])[CH2:28][CH2:27][CH2:26][CH2:25]1

참가 물질

4

반응물 2

HCID 80153CyclopentanemethylamineHCID 589117444-Fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

생성물 1

HCID 588744784-[(Cyclopentylmethyl)amino]-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Following the general procedure for Intermediate 2 using 4-fluoro-3-nitro-N,N-bis(2,2,2-trifluoroethyl)benzamide (122 mg, 0.350 mmol) and cyclopentylmethyl amine (42 mg, 0.420 mmol) in 3 mL of EtOH containing TEA (0.075 mL, 0.525 mmol). The product was purified by flash chromatography on silica gel using 3:1/hexanes:EtOAc as eluent. Yield: 141 mg (94%); 1H NMR (400 MHz, CHLOROFORM-D) δ 1.30 (m, 2H), 1.64 (m, 4H), 1.89 (m, 2H), 2.26 (m, 1H), 3.24 (dd, J=7.23, 5.04 Hz, 2H), 4.23 (q, J=8.42 Hz, 4H), 6.91 (d, J=8.97 Hz, 1H), 7.50 (dd, J=8.97, 2.20 Hz, 1H), 8.26 (d, J=2.20 Hz, 1H), 8.33 (s, 1H); MS (ESI) 427.82 (MH+).

후처리

  1. customThe product was purified by flash chromatography on silica gel using 3:1/hexanes

출처 및 근거

ORD 기록
ord-8f376951b18744d28b1a594f1f70ee4f
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07407968B2

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