Hydrochloric Acid → HCID 11375602, compound

HRID 523826Notes

Reaction equation

HRID 523826 reaction equation
C[O-].[Na+].C(O[C:9]([C:11]1[N:12]=[CH:13][C:14]2[C:19]([C:20]=1[OH:21])=[CH:18][CH:17]=[C:16]([O:22][C:23]1[CH:28]=[CH:27][C:26]([NH:29][S:30]([C:33]3[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=3)(=[O:32])=[O:31])=[CH:25][CH:24]=1)[CH:15]=2)=[O:10])CCC.[NH2:40][CH2:41][C:42]([OH:44])=[O:43].Cl>CO>[OH:21][C:20]1[C:19]2[C:14](=[CH:15][C:16]([O:22][C:23]3[CH:24]=[CH:25][C:26]([NH:29][S:30]([C:33]4[CH:38]=[CH:37][C:36]([CH3:39])=[CH:35][CH:34]=4)(=[O:32])=[O:31])=[CH:27][CH:28]=3)=[CH:17][CH:18]=2)[CH:13]=[N:12][C:11]=1[C:9]([NH:40][CH2:41][C:42]([OH:44])=[O:43])=[O:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10942334Sodium MethoxideHCID 66713115HCID 66713115, compound

Product 1

HCID 11375602HCID 11375602, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1.85 ml of 0.5 M sodium methoxide in methanol was added 42 mg of 4-Hydroxy-7-[4-(toluene-4-sulfonylamino)-phenoxy]-isoquinoline-3-carboxylic acid butyl ester and 70 mg of glycine. The resultant mixture was heated at reflux temperature for 24 hours and then cooled to room temperature. The reaction was poured into a 0.2N HCl aqueous solution and then extracted three times with ethyl acetate. The organic fractions were dried over anhydrous sodium sulfate and concentrated to 41 mg of a white solid; MS (+): m/z 508.10 (M+1).

Workup

  1. temperatureat reflux temperature for 24 hours
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe organic fractions were dried over anhydrous sodium sulfate
  4. concentrationconcentrated to 41 mg of a white solid

Sources & evidence

ORD record
ord-cd840ff984994b4ab6366d8c2711896e
Source dataset
uspto-grants-2016_05
Patent number
US09339527B2

Reaction notes

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