Glycine → HCID 67110338, compound

HRID 409304Notes

Reaction equation

HRID 409304 reaction equation
C(O[C:6]([C:8]1[N:9]=[C:10]([C:32]#[N:33])[C:11]2[C:16]([C:17]=1[OH:18])=[CH:15][C:14]([O:19][C:20]1[CH:21]=[CH:22][C:23]3[O:27][C:26]([N:28]([CH3:30])[CH3:29])=[N:25][C:24]=3[CH:31]=1)=[CH:13][CH:12]=2)=[O:7])CCC.[NH2:34][CH2:35][C:36]([OH:38])=[O:37].C[O-].[Na+].CO>>[C:32]([C:10]1[C:11]2[C:16](=[CH:15][C:14]([O:19][C:20]3[CH:21]=[CH:22][C:23]4[O:27][C:26]([N:28]([CH3:29])[CH3:30])=[N:25][C:24]=4[CH:31]=3)=[CH:13][CH:12]=2)[C:17]([OH:18])=[C:8]([C:6]([NH:34][CH2:35][C:36]([OH:38])=[O:37])=[O:7])[N:9]=1)#[N:33]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 67110108HCID 67110108, compound

Product 1

HCID 67110338HCID 67110338, compoundYield 82%

Procedure

A mixture of 1-cyano-6-(2-dimethylamino-benzooxazol-5-yloxy)-4-hydroxy-isoquinoline-3-carboxylic acid butyl ester (55 mg, 0.12 mmol), glycine (186 mg, 2.47 mmol) and 0.5 M sodium methoxide/methanol (4.7 mL) was refluxed for twenty-five hours before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (35 mL) and washed with dichloromethane (2×25 mL). The remaining aqueous layer was acidified to pH=3 with 1N HCl (3.5 mL). The white precipitate was filtered, washed with water and dried in vacuo to give the title compound as a white solid (44 mg): MS: (+) m/z 448.27 (M+1).

Workup

  1. temperaturewas refluxed for twenty-five hours before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (35 mL)
  4. washwashed with dichloromethane (2×25 mL)
  5. filtrationThe white precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-067525020239416d94bc3589ea778a44
Source dataset
uspto-grants-2014_06
Patent number
US08759373B2

Reaction notes

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