Glycine → HCID 24780835, compound

HRID 409313Notes

Reaction equation

HRID 409313 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:35]#[N:36])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:34]=[CH:33][C:23]3[N:24]=[C:25]([N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)[S:26][C:22]=3[CH:21]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:37][CH2:38][C:39]([OH:41])=[O:40].C[O-].[Na+].CO>>[C:35]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][C:20]3[CH:34]=[CH:33][C:23]4[N:24]=[C:25]([N:27]5[CH2:28][CH2:29][O:30][CH2:31][CH2:32]5)[S:26][C:22]=4[CH:21]=3)=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:37][CH2:38][C:39]([OH:41])=[O:40])=[O:7])[N:9]=1)#[N:36]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 67110404HCID 67110404, compound

Product 1

HCID 24780835HCID 24780835, compoundYield 87.2%

Procedure

A mixture of 1-cyano-4-hydroxy-6-(2-morpholin-4-yl-benzothiazol-6-yloxy)-isoquinoline-3-carboxylic acid butyl ester (137 mg, 0.27 mmol), glycine (408 mg, 5.43 mmol) and 0.5 M sodium methoxide/methanol (10.3 mL) was refluxed for twenty-six hours before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (40 mL) and extracted with dichloromethane (2×35 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (7.5 mL). The white precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (119 mg): MS: (+) m/z 506.26 (M+1); (−) m/z 504.24 (M−1).

Workup

  1. temperaturewas refluxed for twenty-six hours before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (40 mL)
  4. extractionextracted with dichloromethane (2×35 mL)
  5. filtrationThe white precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-038f4fcb568845dea9458956ea0de5f9
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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