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

反応式

HRID 587785 の反応式
[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]

参加物

8

反応物 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

生成物 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)benzamide収率 74%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-5effbdbfd3ee4ea58f83c8678e4cf775
出典データセット
uspto-grants-2016_01
特許番号
US09226501B2

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