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Methanol → (R)-N-(6-Chloro-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

HRID 1161277
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HRID 1161277 반응식
C([O:4][CH2:5][C@H:6]([N:8]1[CH:17]=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:33])[C:14]=2[NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=2)[C:9]1=[O:34])[CH3:7])(=O)C.C(=O)([O-])[O-].[K+].[K+].CO>O>[Cl:33][C:13]1[C:14]([NH:18][C:19](=[O:32])[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[C:23]([C:28]([F:30])([F:31])[F:29])[CH:22]=2)=[C:15]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:34])[N:8]([C@H:6]([CH3:7])[CH2:5][OH:4])[CH:17]=[CH:16]2
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참가 물질

5

반응물 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 59515708(R)-2-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate

생성물 1

HCID 16742552(R)-N-(6-Chloro-2-(1-hydroxypropan-2-yl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide수율 65.7%

시약·촉매·용매 1

HCID 962
Water
촉매

실험 절차

A round bottom flask was charged with (R)-2-(6-chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)propyl acetate (250 mg, 0.00050 mol), potassium carbonate (100 mg, 0.00075 mol) and methanol (8 mL, 0.2 mol) and 2 drops of water. The reaction was stirred at room temperature for 30 minutes. The reaction mixture was filtered, washed with methanol. The solvent was removed and the residue purified by preparative HPLC (reverse phase) to obtain the product as an off white solid (about 150 mg). MS m/z=457.4 (M+1). 1H NMR (400 MHz; DMSO) δ 10.17 (s, 1H), 8.16 (d, J=8.85 Hz, 1H), 7.82 (d, J=7.76 Hz, 1H), 7.72-7.74 (m, 1H), 7.59 (d, J=8.84 Hz, 1H), 7.54-7.49 (m, 2H), 6.42 (d, J=7.50 Hz, 1H), 5.03-4.93 (m, 2H), 3.90 (s, 2H), 3.66-3.56 (m, 2H), 1.28 (d, J=7.63 Hz, 3H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. washwashed with methanol
  3. customThe solvent was removed
  4. customthe residue purified by preparative HPLC (reverse phase)

출처 및 근거

ORD 기록
ord-d6dd0c5166154942b1c8142b9f265cea
출처 데이터셋
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07816371B2

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