N-methyl-2-pyrrolidone → 2-{4-[(S)-7-(3-Fluoro-propyl)-2,7-diaza-spiro[4.4]non-2-yl]-phenyl}-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

HRID 69442

반응식

HRID 69442 반응식
[CH2:1]1[C@@:5]2([CH2:9][CH2:8][NH:7][CH2:6]2)[CH2:4][CH2:3][N:2]1[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH2:25][CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=3)[C:17]2=[O:27])=[CH:12][CH:11]=1.Br[CH2:29][CH2:30][CH2:31][F:32].C(=O)([O-])O.[Na+].CN1C(=O)CCC1>O.C(OCC)(=O)C>[F:32][CH2:31][CH2:30][CH2:29][N:7]1[CH2:8][CH2:9][C@@:5]2([CH2:1][N:2]([C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:25][CH2:24][C:23]5[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=5)[C:17]4=[O:27])=[CH:12][CH:11]=3)[CH2:3][CH2:4]2)[CH2:6]1

참가 물질

7

반응물 4

HCID 13387N-methyl-2-pyrrolidoneHCID 67699Propane, 1-bromo-3-fluoro-HCID 516892Sodium BicarbonateHCID 689918082-[(S)-4-(2,7-Diaza-spiro[4.4]non-2-yl)-phenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

생성물 1

HCID 689903662-{4-[(S)-7-(3-Fluoro-propyl)-2,7-diaza-spiro[4.4]non-2-yl]-phenyl}-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

A mixture of 2-[(S)-4-(2,7-diaza-spiro[4.4]non-2-yl)-phenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (0.20 g), 1-bromo-3-fluoro-propane (76 mg), sodium hydrogencarbonate (10 mg) and NMP (5 mL) was heated at 50° C. for 15 hours. The reaction mixture was distributed between ethyl acetate and water. The organic phase was dried over magnesium sulfate and concentrated. The raw product was purified by preparative HPLC. In this way the product was obtained with molecular weight 423.54 (C25H30FN3O2); MS (ESI): 424 (M+H+).

후처리

  1. dry with materialThe organic phase was dried over magnesium sulfate
  2. concentrationconcentrated
  3. customThe raw product was purified by preparative HPLC
  4. customIn this way the product was obtained with molecular weight 423.54 (C25H30FN3O2)

출처 및 근거

ORD 기록
ord-66e9a8fd87d04aea8e26a46ce96c38f2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822495B2

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