Beta-Alanine → 3-[(4-Hydroxy-1-methyl-7 phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid

HRID 1481117

반응식

HRID 1481117 반응식
CO[C:3]([C:5]1[N:6]=[C:7]([CH3:23])[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].[NH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28].C[O-].[Na+].CO>>[OH:15][C:14]1[C:13]2[C:8](=[CH:9][C:10]([O:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:11][CH:12]=2)[C:7]([CH3:23])=[N:6][C:5]=1[C:3]([NH:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[O:4]

참가 물질

4

반응물 3

HCID 239Beta-AlanineHCID 23694274Sodium methanolate methanolHCID 712448953-Isoquinolinecarboxylic acid, 4-hydroxy-1-methyl-7-phenoxy-, methyl ester

생성물 1

HCID 898128553-[(4-Hydroxy-1-methyl-7 phenoxy-isoquinoline-3-carbonyl)-amino]-propionic acid수율 82.1%

실험 절차

A mixture of 4-hydroxy-1-methyl-7-phenoxy-isoquinoline-3-carboxylic acid methyl ester (120 mg, 0.39 mmol) and beta-alanine (242 mg, 2.72 mmol) in 0.5 M NaOMe/MeOH solution (4.5 mL, 2.25 mmol) was microwaved at 120° C. for 30 min. Reaction mixture was concentrated and dissolved in water (100 mL). It was acidified by 1 N HCl to pH=3-4. Gummy precipitate was collected by filtration and dissolved in EtOAc. It was dried over MgSO4, filtered and concentrated to provide the title compound 116 mg (0.32 mmol) in 81% yield. LC-MS ESI−: 365.16 (M−1)−.

후처리

  1. customwas microwaved at 120° C. for 30 min
  2. customReaction mixture
  3. concentrationwas concentrated
  4. dissolutiondissolved in water (100 mL)
  5. filtrationGummy precipitate was collected by filtration
  6. dissolutiondissolved in EtOAc
  7. dry with materialIt was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a8b543e6e47b4103b198a565651bca07
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409892B2

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