Hydrochloric Acid → HCID 71736596, compound

HRID 1481206Notes

Reaction equation

HRID 1481206 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:28]#[N:29])[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.[NH2:30][CH2:31][C:32]1([C:36]([OH:38])=[O:37])[CH2:35][CH2:34][CH2:33]1.C[O-].[Na+].[OH-].[Na+].Cl>C(O)C.O>[C:28]([C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[C:13]([S:19]([CH:22]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)(=[O:20])=[O:21])[CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:30][CH2:31][C:32]2([C:36]([OH:38])=[O:37])[CH2:35][CH2:34][CH2:33]2)=[O:7])[N:9]=1)#[N:29]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10942334Sodium MethoxideHCID 23405971HCID 23405971, compoundHCID 89812859HCID 89812859, compound

Product 1

HCID 71736596HCID 71736596, compoundYield 19.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 1-cyano-7-cyclohexanesulfonyl-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (30 mg, 0.072 mmol) and 1-aminomethyl-cyclobutanecarboxylic acid (48 mg, 0.29 mmol) (available from Ukrorgsyntez Ltd) in ethanol (0.7 mL) was added NaOMe solid (16 mg, 0.29 mmol). The resultant mixture was microwaved at 140° C. for 1 h. The reaction mixture was then treated with 1 mL of 3 N NaOH aqueous solution and stirred at room temperature for 3 h. Reaction mixture was diluted with water (60 mL) and acidified by 1 N HCl to pH=3-4. Precipitate was collected and purified by silica gel chromatography, eluting with 0-10% MeOH/CH2Cl2 to provide the title compound 6.4 mg (0.014 mmol) in 19% yield. LC-MS ESI−: 470.12 (M−1)−.

Workup

  1. customReaction mixture
  2. customPrecipitate was collected
  3. custompurified by silica gel chromatography
  4. washeluting with 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-41c765d54605450a8c7505e3cde4352d
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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