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Potassium Carbonate → N-(6-Chloro-2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

HRID 1161297
ノート
印刷プレビュー

反応式

HRID 1161297 の反応式
C([O:4][CH2:5][CH2:6][N:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([Cl:32])[C:13]=2[NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:30])([F:29])[F:28])[CH:21]=2)[C:8]1=[O:33])(=O)C.C(=O)([O-])[O-].[K+].[K+]>O.CO>[Cl:32][C:12]1[C:13]([NH:17][C:18](=[O:31])[CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([C:27]([F:29])([F:30])[F:28])[CH:21]=2)=[C:14]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:33])[N:7]([CH2:6][CH2:5][OH:4])[CH:16]=[CH:15]2
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 11430Potassium CarbonateHCID 595158712-(6-Chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate

生成物 1

HCID 24760888N-(6-Chloro-2-(2-hydroxyethyl)-1-oxo-1,2-dihydroisoquinolin-5-yl)-2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamide

試薬・触媒・溶媒 2

HCID 962Water触媒HCID 887Methanol
溶媒

実験手順

A round bottom flask was charged with 2-(6-chloro-5-(2-(4-fluoro-3-(trifluoromethyl)phenyl)acetamido)-1-oxoisoquinolin-2(1H)-yl)ethyl acetate (80.0 mg, 0.000165 mol), potassium carbonate (34.2 mg, 0.000248 mol), methanol and 2 drops of water and the reaction stirred for 20 minutes at room temperature. The reaction was then filtered over sodium sulfate and celite and washed with methanol. The solvent was removed and the residue purified by preparative HPLC (reverse phase) to obtain the product as a pale yellow solid. MS m/z=443.3 (M+H) 1H NMR (400 MHz; DMSO-d6) δ 10.18 (s, 1H), 8.15 (d, J=8.81 Hz, 1H), 7.82 (d, J=6.7 Hz, 1H), 7.77-7.74 (m, 1H), 7.59 (d, J=8.81 Hz, 1H), 7.52 (t, J=9.52 Hz, 1H), 7.46 (d, J=7.40 Hz, 1H), 6.40 (d, J=7.59 Hz, 1H), 4.88 (t, J=5.0 Hz, 1H), 4.00 (t, J=5.55 Hz, 2H), 3.89 (s, 2H), 3.65 (q, J=5.55 Hz, 2H).

後処理

  1. filtrationThe reaction was then filtered over sodium sulfate and celite
  2. washwashed with methanol
  3. customThe solvent was removed
  4. customthe residue purified by preparative HPLC (reverse phase)

出典と根拠

ORDレコード
ord-caab95ee7e1a4112bf4cfbea92b5388c
出典データセット
uspto-grants-2010_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07816371B2

反応ノート

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