Diethyl Pyrocarbonate → 2-[(4-chlorophenyl)sulfonyl-ethyl-amino]-N-[[2-morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

HRID 1479832ノート

反応式

HRID 1479832 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:17][CH3:18])[C:12](=[CH2:16])[C:13]([OH:15])=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[O:30]1[CH2:35][CH2:34][N:33]([C:36]2[CH:41]=[C:40]([CH2:42][NH2:43])[CH:39]=[C:38]([C:44]3[CH:49]=[CH:48][C:47]([O:50][C:51]([F:54])([F:53])[F:52])=[CH:46][CH:45]=3)[N:37]=2)[CH2:32][CH2:31]1>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH2:17][CH3:18])[C:12](=[CH2:16])[C:13]([NH:43][CH2:42][C:40]2[CH:39]=[C:38]([C:44]3[CH:49]=[CH:48][C:47]([O:50][C:51]([F:54])([F:52])[F:53])=[CH:46][CH:45]=3)[N:37]=[C:36]([N:33]3[CH2:32][CH2:31][O:30][CH2:35][CH2:34]3)[CH:41]=2)=[O:15])(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 1317365862-[(4-Chlorophenyl)sulfonyl-ethyl-amino]prop-2-enoic acidHCID 131736588[2-Morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine

生成物 1

HCID 783205292-[(4-chlorophenyl)sulfonyl-ethyl-amino]-N-[[2-morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide収率 22.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Acid 4D (289.74 mg, 1 mmol) was dissolved in 10 ml of THF and at rt DEPC (1.1 equiv, 0.15 ml) and [2-morpholino-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 27D (1.1 equiv., 388 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (3:7 EtOAc:petroleum ether) afforded 140 mg of a pale yellow solid. Yield=22% 1HNMR (DMSO, 400 MHz) δ 1.15 (3H, t), 3.38 (2H, q), 3.50 (4H, m), 3.70 (4H, m), 4.40 (2H, d), 5.20 (1H, s), 6.18 (1H, s), 6.80 (1H, s), 7.20 (1H, s), 7.42 (2H, d), 7.76 (2H, d), 7.82 (2H, d), 8.18 (2H, d), 8.89 (1H, bt) [M+1] 626.9 (C28H28ClF3N4O5S requires 625.06).

後処理

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionThe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (3:7 EtOAc:petroleum ether)

出典と根拠

ORDレコード
ord-a303ede3639b47d5904830bad0c67857
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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