Ethanol, 2,2,2-trifluoro-, sodium salt (1:1) → (S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(2,2,2-trifluoroethoxy)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

HRID 2422557노트

반응식

HRID 2422557 반응식
Cl[C:2]1[CH:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][C:6]([CH2:19][N:20]3[CH:24]=[C:23]([C@@:25]([OH:32])([CH2:30][CH3:31])[C:26]([F:29])([F:28])[F:27])[N:22]=[N:21]3)=[CH:7][CH:8]=2)[N:3]=1.[F:33][C:34]([F:38])([F:37])[CH2:35][O-:36].[Na+]>CN(C=O)C>[F:27][C:26]([F:29])([F:28])[C@:25]([C:23]1[N:22]=[N:21][N:20]([CH2:19][C:6]2[CH:5]=[C:4]3[C:9]([C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[CH:11][C:2]([O:36][CH2:35][C:34]([F:38])([F:37])[F:33])=[N:3]3)=[CH:8][CH:7]=2)[CH:24]=1)([OH:32])[CH2:30][CH3:31]

참가 물질

4

반응물 2

HCID 23677971Ethanol, 2,2,2-trifluoro-, sodium salt (1:1)HCID 86621982(S)-2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol

생성물 1

HCID 86621984(S)-1,1,1-trifluoro-2-(1-{[4-(4-fluorophenyl)-2-(2,2,2-trifluoroethoxy)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)butan-2-ol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of (S)-2-(1-{[2-chloro-4-(4-fluorophenyl)quinolin-7-yl]methyl}-1H-1,2,3-triazol-4-yl)-1,1,1-trifluorobutan-2-ol (60 mg, 0.13 mmol) and sodium trifluoroethoxide (79 mg, 0.65 mmol) in DMF (3 mL) was stirred at 120° C. for 1.5 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated under reduce pressure. Purification on silica gel (eluting with ethyl acetate/hexanes, 3:7) gave the title compound. MS (+ESI): 529 (M+H)+.

후처리

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification on silica gel (eluting with ethyl acetate/hexanes, 3:7)

출처 및 근거

ORD 기록
ord-fbdb645ff75f4c76828ab1fae9232fac
출처 데이터셋
uspto-grants-2011_06
특허 번호
US07960409B2

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