Hydrochloric Acid → {1-[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-cyclohexyl}-acetic acid

HRID 1481097

반응식

HRID 1481097 반응식
CO[C:3]([C:5]1[N:6]=[C:7]([C:23]#[N:24])[C:8]2[C:13]([C:14]=1[OH:15])=[CH:12][CH:11]=[C:10]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:9]=2)=[O:4].[NH2:25][C:26]1([CH2:32][C:33]([OH:35])=[O:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1.C[O-].[Na+].Cl>CN(C=O)C.O>[C:23]([C:7]1[C:8]2[C:13](=[CH:12][CH:11]=[C:10]([O:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:9]=2)[C:14]([OH:15])=[C:5]([C:3]([NH:25][C:26]2([CH2:32][C:33]([OH:35])=[O:34])[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)=[O:4])[N:6]=1)#[N:24]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 44266932-(1-Aminocyclohexyl)acetic acid hydrochlorideHCID 10942334Sodium MethoxideHCID 89812860HCID 89812860, 화합물

생성물 1

HCID 89813070{1-[(1-Cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carbonyl)-amino]-cyclohexyl}-acetic acid수율 20,000%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 1-cyano-4-hydroxy-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (100 mg, 0.3 μmol) and (1-amino-cyclohexyl)-acetic acid (245 mg, 1.56 mmol) (Matrix Scientific, Columbia S.C.) in 3 mL of DMF was added NaOMe solid (67 mg, 1.25 mmol). The resultant mixture was heated in a 150° C. oil bath for 7 h. Reaction mixture was diluted with water (100 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected, dried and the purified by silica gel chromatography, eluting with 10-70% EtOAc/hexanes to provide the title compound 27 mg (0.06 mmol) in 19% yield. LC-MS ESI−: 443.95 (M−1)−.

후처리

  1. customReaction mixture
  2. customPrecipitate was collected
  3. customdried
  4. customthe purified by silica gel chromatography
  5. washeluting with 10-70% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-49f026dd04434b40979ce8c2df84770c
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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