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Acetic Acid → Methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate

HRID 2104514
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HRID 2104514 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.[CH3:30][O:31][C:32](=[O:42])[CH2:33][C:34]1[CH:39]=[CH:38][C:37]([CH:40]=O)=[CH:36][CH:35]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C>C1COCC1>[C:22]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[C:4]1[CH:3]=[C:2]([NH:1][CH2:40][C:37]3[CH:36]=[CH:35][C:34]([CH2:33][C:32]([O:31][CH3:30])=[O:42])=[CH:39][CH:38]=3)[CH:7]=[CH:6][CH:5]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1
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참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11326798[4-(3-Aminophenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)MethanoneHCID 19363032Methyl 2-(4-formylphenyl)acetate

생성물 1

HCID 16718795Methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate수율 56.4%

시약·촉매·용매

1
HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

[4-(3-Aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone (0.39 g, 1.0 mmol) and (4-formyl-phenyl)-acetic acid methyl ester (0.17 g, 0.96 mmol) were mixed in THF (15 mL) and then treated with NaBH(OAc)3 (0.43 g, 2.0 mml) and acetic acid (0.5 mL). After stirring at 40° C. under a N2 atmosphere for 2 h the mixture was quenched with water and then extracted with ethyl acetate. The organic residue was purified by silica gel chromatography using 5-50% EtOAc/hexanes as eluent to provide methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate as an orange solid (0.30 g, 54%): MS (EI) m/z 555.3 (M+H)+; 1H NMR (DMSO-d6): δ 3.61 (s, 3H), 3.66 (s, 2H), 4.12 (d, J=6.0 Hz, 2H), 6.40 (d, J=6.8 Hz, 2H), 6.49 (d, J=6.8 Hz, 2H), 6.98 (t, J=7.7 Hz, 1H), 7.18-7.22 (m, 4H), 7.36 (t, J=7.5 Hz, 2H), 7.55 (t, J=7.4 Hz, 1H), 7.59 (d, J=9.0 Hz, 2H), 7.72 (t, J=8.6 Hz, 1H), 7.99 (d, J=8.5 Hz, 1H), 8.30 (d, J=7.3 Hz, 1H), 9.08 (s, 1H).

후처리

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. customThe organic residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-db468764b3d0410690623b753dcec760
출처 데이터셋
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07576215B2

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