1,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate → 3-[5-(5-{3-Cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acid

HRID 2192533노트

반응식

HRID 2192533 반응식
[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[CH:22][N:23]=[C:24]4[CH2:29][CH2:30][C:31]([O:33]C(C)(C)C)=[O:32])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:13][CH2:12]1)#[N:2]>Cl.O1CCOCC1.CN1CCCC1=O>[C:1]([C:3]1[CH:4]=[C:5]([C:14]2[O:18][N:17]=[C:16]([C:19]3[CH:28]=[CH:27][CH:26]=[C:25]4[C:20]=3[CH:21]=[CH:22][N:23]=[C:24]4[CH2:29][CH2:30][C:31]([OH:33])=[O:32])[N:15]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH2:10][CH:11]1[CH2:13][CH2:12]1)#[N:2]

참가 물질

5

반응물 1

HCID 668773731,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate

생성물 1

HCID 444766733-[5-(5-{3-Cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoic acid수율 33.1%

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 13387N-methyl-2-pyrrolidone용매HCID 312751,4-Dioxane용매

실험 절차

1,1-Dimethylethyl 3-[5-(5-{3-cyano-4-[(cyclopropylmethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-isoquinolinyl]propanoate (D48; 36 mg, 0.072 mmol) was dissolved in 4N HCl in 1,4-dioxane (4 ml) and the mixture was allowed to stand at room temperature for 4.5 h. The solvent was evaporated in vacuo and the residue triturated with dry ether to give a white solid which was dissolved in N-methyl-2-pyrrolidinone (1 ml) and purified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column, eluting with solvents A/B (A: Water+0.1% Formic acid, B: MeCN:Water 95:5+0.05% Formic acid)). The solvent was dried under a stream of nitrogen to give the title compound as a white solid (10.5 mg)

후처리

  1. customThe solvent was evaporated in vacuo
  2. customthe residue triturated with dry ether
  3. customto give a white solid which
  4. custompurified by Mass Directed Preparative HPLC (Supelcosil ABZ+Plus column
  5. washeluting with solvents A/B (A: Water+0.1% Formic acid, B
  6. customThe solvent was dried under a stream of nitrogen

출처 및 근거

ORD 기록
ord-95350a07e7b243f4bd751b74783c9c5c
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329730B2

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