Diethyl Pyrocarbonate → 1-[(4-fluorophenyl)sulfonylamino]-N-[[2-pyrrolidin-1-yl-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]cyclopropanecarboxamide

HRID 1479856ノート

反応式

HRID 1479856 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2([C:15]([OH:17])=O)[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[N:29]1([C:34]2[CH:39]=[C:38]([CH2:40][NH2:41])[CH:37]=[C:36]([C:42]3[CH:47]=[CH:46][C:45]([O:48][C:49]([F:52])([F:51])[F:50])=[CH:44][CH:43]=3)[N:35]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][C:12]2([C:15]([NH:41][CH2:40][C:38]3[CH:37]=[C:36]([C:42]4[CH:43]=[CH:44][C:45]([O:48][C:49]([F:52])([F:50])[F:51])=[CH:46][CH:47]=4)[N:35]=[C:34]([N:29]4[CH2:33][CH2:32][CH2:31][CH2:30]4)[CH:39]=3)=[O:17])[CH2:13][CH2:14]2)(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 607292541-[(4-Fluorophenyl)sulfonylamino]cyclopropanecarboxylic acidHCID 131736589[2-Pyrrolidin-1-yl-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine

生成物 1

HCID 903841731-[(4-fluorophenyl)sulfonylamino]-N-[[2-pyrrolidin-1-yl-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]cyclopropanecarboxamide収率 22.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Acid 15C (260 mg, 1 mmol) was dissolved in 5 ml of THF and at rt DEPC (1.1 equiv, 0.17 ml) and [2-pyrrolidin-1-yl-6-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methanamine 27C (1.1 equiv., 371 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in EtOAc (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 130 mg of a white solid. Yield=22% 1HNMR (DMSO, 200 MHz) δ 0.71 (2H, bm), 1.08 (2H, bm), 1.92 (4H, m), 3.47 (4H, m), 4.29 (2H, d, J=5.6 Hz), 6.41 (1H, s), 7.09 (1H, s), 7.45 (4H, m), 7.82 (2H, m), 8.17 (2H, d, J=9 Hz), 8.38 (1H, t), 8.71 (1H, bs) [M+1] 579.4 (C27H26F4N4O4S requires 578.58).

後処理

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionThe residue was dissolved in EtOAc (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-3243b1291ad445858832473beedca6a0
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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