Diethyl Pyrocarbonate → N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-2,3-dihydro-2-oxobenzo[d]oxazole-4-carboxamide

HRID 1505203ノート

反応式

HRID 1505203 の反応式
[O:1]=[C:2]1[NH:6][C:5]2=[C:7]([C:11]([OH:13])=O)[CH:8]=[CH:9][CH:10]=[C:4]2[O:3]1.CCOC(OC(OCC)=O)=O.[F:25][C:26]([F:42])([F:41])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH2:34])=[C:29]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:28]=1>C1COCC1>[F:41][C:26]([F:25])([F:42])[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][NH:34][C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:4]3[O:3][C:2](=[O:1])[NH:6][C:5]=23)=[O:13])=[C:29]([N:35]2[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]2)[CH:28]=1

参加物

5

反応物 3

HCID 3051Diethyl PyrocarbonateHCID 109210912-Oxo-2,3-dihydro-1,3-benzoxazole-4-carboxylic acidHCID 58873623(4-(Trifluoromethyl)-2-(piperidin-1-yl)phenyl)-methanamine

生成物 1

HCID 53476934N-(4-(trifluoromethyl)-2-(piperidin-1-yl)benzyl)-2,3-dihydro-2-oxobenzo[d]oxazole-4-carboxamide収率 19.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

2,3-dihydro-2-oxobenzo[d]oxazole-4-carboxylic acid 21 (560 mg, 3.1 mmol) was dissolved in 20 ml of THF and at 0° C. DEPC (0.55 ml, 1.2 equiv) and amine 2c (964 mg, 1.2 equiv.) were added to the solution. The mixture was warmed at 80° C. overnight, then evaporated and the crude 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 residue by chromatographic column using AcOEt 4/petroleum ether 6 as eluant gave 250 mg of a pale yellow solid. Yield=19% 1HNMR (DMSO, 200 MHz) δ 4.58 (2H, d, J=5.8 Hz), 7.14 (1H, t, J=8 Hz), 7.41 (4H, m), 7.68 (1H, dd, J=8 Hz, J′=0.8 Hz), 9.20 (1H, bt), 11.59 (1H, bs); [M+1] 420.2 (C21H20F3N3O3 requires 419.4).

後処理

  1. customevaporated
  2. dissolutionthe crude was dissolved in AcOEt (30 ml)
  3. washwashed with water (1×20 ml) and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe purification of the crude residue by chromatographic column

出典と根拠

ORDレコード
ord-3a51ea9d376f4d6ba0dd798276c379d9
出典データセット
uspto-grants-2015_12
特許番号
US09216975B2

反応ノート

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