Beta-Alanine → HCID 71735620, compound

HRID 1481161Notes

Reaction equation

HRID 1481161 reaction equation
C(O[C:6]([C:8]1[N:9]=[CH:10][C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][CH:14]=[C:13]([S:19]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)(=[O:21])=[O:20])[CH:12]=2)=[O:7])CCC.[NH2:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32].C[O-].[Na+].CO.Cl>O>[CH:22]1([S:19]([C:13]2[CH:12]=[C:11]3[C:16]([C:17]([OH:18])=[C:8]([C:6]([NH:28][CH2:29][CH2:30][C:31]([OH:33])=[O:32])=[O:7])[N:9]=[CH:10]3)=[CH:15][CH:14]=2)(=[O:20])=[O:21])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 239Beta-AlanineHCID 313Hydrochloric AcidHCID 23694274Sodium methanolate methanolHCID 66713137HCID 66713137, compound

Product 1

HCID 71735620HCID 71735620, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 7-cyclohexanesulfonyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (20 mg, 0.05 mmol) (prepared according to U.S. Pat. No. 7,629,357) and beta-alanine (45 mg, 0.5 mmol) in 0.5 M NaOMe/MeOH (0.8 mL, 0.4 mmol) was microwaved at 120° C. for 30 min. Reaction mixture was diluted with water (50 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected, rinsed with water and dried in vacuo to provide the title compound 9.4 mg (0.023 mmol) in 46% yield. LC-MS ESI−: 405.05 (M−1)−.

Workup

  1. customprepared
  2. customReaction mixture
  3. customPrecipitate was collected
  4. washrinsed with water
  5. customdried in vacuo

Sources & evidence

ORD record
ord-0a67fc7fb77c4729960d768aca1d4c19
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

Loading…