Acetic Acid → 6-Methoxy-5-({[4-(trifluoromethoxy)benzyl]amino}methyl)-2-naphthoic acid methyl ester

HRID 23228

반응식

HRID 23228 반응식
[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[C:11]=2[CH:15]=O)[CH:6]=1)=[O:4].[F:19][C:20]([F:31])([F:30])[O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1.CC(O)=O.C([BH3-])#N.[Na+]>CCO>[CH3:1][O:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:17][CH3:18])[C:11]=2[CH2:15][NH:27][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][C:20]([F:19])([F:30])[F:31])=[CH:23][CH:24]=2)[CH:6]=1)=[O:4]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5718464-(Trifluoromethoxy)benzylamineHCID 5003444Sodium cyanoborohydrideHCID 118068606-Methoxy-5-formyl-2-naphthoic acid methyl ester

생성물 1

HCID 697331386-Methoxy-5-({[4-(trifluoromethoxy)benzyl]amino}methyl)-2-naphthoic acid methyl ester수율 42%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 6-methoxy-5-formyl-2-naphthoic acid methyl ester (1.09 g, 4.46 mmol) in EtOH (40 mL) at room temperature was added 4-trifluoromethoxy-benzyl amine (0.749 mL, 4.91 mmol) followed by HOAc (0.255 mL, 4.46 mmol). After 10 min. at this temperature, sodium cyanoborohydride (0.420 g, 6.69 mmol) was added, and reaction was continued stirring at rt for 4 h. After 1 h at this temperature, the reaction was heated to 45° C. for 2 h. The solution was quenched with sat. aq. NaHCO3 (20 mL) and then extracted with EtOAc (200 mL). The organic layer was washed with brine (20 mL) and dried (MgSO4). After concentration, the residue was purified by flash chromatography (0 to 10% MeOH:CHCl3 gradient) to afford the product (0.780 g, 42%) as a solid; 1H NMR (DMSO-d6) δ3.77 (s, 2H), 3.86 (s, 3H), 3.88 (s, 3H), 4.07 (s, 2H), 7.26 (d, J =8.0 Hz, 2H), 7.44 (d, J=8.6 Hz, 2H), 7.48 (d, J=9.2 Hz, 1H), 7.88 (dd, J=1.9, 8.9 Hz, 1H), 8.06 (d, J=5.2 Hz, 1H), 8.08 (d, J=5.3 Hz, 1H), 8.52 (d, J=1.7 Hz, 1H); mass spectrum [(+) El], m/z 420 (M+H)+.

후처리

  1. customreaction
  2. waitAfter 1 h at this temperature
  3. temperaturethe reaction was heated to 45° C. for 2 h
  4. customThe solution was quenched with sat. aq. NaHCO3 (20 mL)
  5. extractionextracted with EtOAc (200 mL)
  6. washThe organic layer was washed with brine (20 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationAfter concentration
  9. customthe residue was purified by flash chromatography (0 to 10% MeOH:CHCl3 gradient)

출처 및 근거

ORD 기록
ord-5f4aae98621c43a4ab8358138b73fa10
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849761B2

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