Acetic Acid → 2-Cyclopentyl-N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamide

HRID 1820153ノート

反応式

HRID 1820153 の反応式
[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([NH:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)=[CH:12][C:11]=2[CH3:29])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:30](O)(=O)C.C([BH3-])#N.[Na+].C=O>CO>[CH:1]1([CH2:6][C:7]([NH:9][C:10]2[C:15]([CH3:16])=[CH:14][C:13]([N:17]([CH3:30])[CH2:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][CH:20]=3)=[CH:12][C:11]=2[CH3:29])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 115169952-Cyclopentyl-N-[2,6-dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamide

生成物 1

HCID 116185902-Cyclopentyl-N-{2,6-dimethyl-4-[methyl-(4-trifluoromethyl-benzyl)-amino]-phenyl}-acetamide収率 97%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
25 °C

実験手順

To 2-cyclopentyl-N-[2,6-dimethyl-4-(4-trifluoromethyl-benzylamino)-phenyl]-acetamide (4k, 150 mg) dissolved in methanol (20 mL) and acetic acid (2 mL) were added sodium cyanoborohydride (175 mg) and formaldehyde (200 uL) and the reaction mixture was stirred at 25° C. for 70 minutes. The reaction was quenched with saturated aqueous sodium bicarbonate and the product collected by filtration to furnish 151 mg (97% yield) of the title compound as a white solid. LC-MS (m/z) 419 (MH+); tR=3.39, (UV, ELSD) 99%, 99%. 1H NMR (500 MHz, DMSO-d6): 1.20 (m, 2H), 1.51 (m, 2H), 1.61 (m, 2H), 1.75 (m, 2H), 2.02 (s, 6H), 2.24 (m, 3H), 2.97 (s, 3H), 4.63 (s, 2H), 6.42 (s, 2H), 7.41 (d, 2H), 7.68 (d, 2H), 8.83 (s, 1H).

後処理

  1. customThe reaction was quenched with saturated aqueous sodium bicarbonate
  2. filtrationthe product collected by filtration

出典と根拠

ORDレコード
ord-8b8a393a11444f28b76bdbfa5c946a15
出典データセット
uspto-grants-2009_10
特許番号
US07601870B2

反応ノート

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