Diisopropylethylamine → (E)-2-Amino-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamide

HRID 587785

반응식

HRID 587785 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:34]([F:37])([F:36])[F:35])/[CH:11]=[CH:12]/[C:13]2[CH:30]=[CH:29][C:16]([C:17]([NH:19][CH2:20][C:21](=[O:28])[NH:22][CH2:23][C:24]([F:27])([F:26])[F:25])=[O:18])=[C:15]([N+:31]([O-])=O)[CH:14]=2)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].Cl.NCC(NCC(F)(F)F)=O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.ClC1C=C(C(C(F)(F)F)/C=C/C2C=CC(C(O)=O)=C([N+]([O-])=O)C=2)C=C(Cl)C=1F>C(Cl)Cl.O>[NH2:31][C:15]1[CH:14]=[C:13](/[CH:12]=[CH:11]/[CH:10]([C:4]2[CH:5]=[C:6]([Cl:9])[C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)[C:34]([F:35])([F:36])[F:37])[CH:30]=[CH:29][C:16]=1[C:17]([NH:19][CH2:20][C:21](=[O:28])[NH:22][CH2:23][C:24]([F:25])([F:26])[F:27])=[O:18]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 429136982-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride (1:1)HCID 86722763(E)-4-(3-(3,5-Dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-nitrobenzoic acidHCID 86722764(E)-4-(3-(3,5-Dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-nitro-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamide

생성물 1

HCID 86722765(E)-2-Amino-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamide수율 74%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

(E)-4-(3-(3,5-Dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-nitro-N-(2-oxo-2-(2,2,2-trifluoroethylamino)ethyl)benzamide: 2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride (96 mg, 0.35 mmol), PyBOP (165 mg, 0.32 mmol) and DIPEA (0.1 mL, 0.57 mmol) were added to a stirred solution of (E)-4-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-2-nitrobenzoic acid (130 mg, 0.29 mmol) in CH2Cl2 (3 mL) and the reaction mixture was stirred at ambient temperature for 8 h. Water was added to reaction mixture and extracted with CH2Cl2. The organic layer was washed with brine, dried (Na2SO4), filtered, concentrated and the residue was purified by column chromatography on silica (100-200 mesh) eluting with 30% EtOAc in petroleum ether to afford the title compound as a yellow solid (120 mg, 74%): 1H NMR (300 MHz, DMSO-d6) δ 9.04 (t, J=5.7 Hz, 1H), 8.60 (t, J=6.0 Hz, 1H), 8.25 (s, 1H), 7.97-7.94 (m, 1H), 7.87 (d, J=6.3 Hz, 2H), 7.69 (d, J=7.5 Hz, 1H), 7.15 (dd, J=15.9, 9.3 Hz, 1H), 6.89 (d, J=15.9 Hz, 1H), 4.88-4.83 (m, 1H), 3.98-3.89 (m, 4H); ESIMS m/z 575.87 ([M+H]+); IR (KBr) 3430, 2925, 1663, 1168, 832 cm−1.

후처리

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by column chromatography on silica (100-200 mesh)
  7. washeluting with 30% EtOAc in petroleum ether

출처 및 근거

ORD 기록
ord-5effbdbfd3ee4ea58f83c8678e4cf775
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09226501B2

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