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

HRID 1820153노트

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HRID 1820153 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

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온도
25 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-8b8a393a11444f28b76bdbfa5c946a15
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601870B2

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