Glycine → HCID 24757335, compound

HRID 642361Notes

Reaction equation

HRID 642361 reaction equation
C(O[C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([F:21])=[C:17]([Cl:22])[CH:16]=3)[S:14][C:8]=2[C:7]=1[OH:23])=[O:5])C.[NH2:24][CH2:25][C:26]([OH:28])=[O:27].C[O-].[Na+].CO>>[Cl:22][C:17]1[CH:16]=[C:15]([C:13]2[S:14][C:8]3[C:7]([OH:23])=[C:6]([C:4]([NH:24][CH2:25][C:26]([OH:28])=[O:27])=[O:5])[N:11]=[CH:10][C:9]=3[N:12]=2)[CH:20]=[CH:19][C:18]=1[F:21]

Participants

4

Reactant 3

HCID 750GlycineHCID 23694274Sodium methanolate methanolHCID 68426276HCID 68426276, compound

Product 1

HCID 24757335HCID 24757335, compoundYield 52.4%

Procedure

A mixture of 2-(3-chloro-4-fluoro-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (101 mg, 0.29 mmole) and glycine (429 mg, 5.72 mmole) in 0.5 M sodium methoxide/methanol (10.9 ml, 5.43 mmole) was refluxed for 4 days before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (100 ml) and extracted with dichloromethane (3×50 ml). The remaining aqueous layer was acidified to pH=3 with 1N HCl (6.5 ml). The resulting precipitate was filtered, washed with water and dried in vacuo to give the title compound as a brown solid (58 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.50 (br s, 1H), 8.89 (s, 1H), 8.36 (m, 1H), 8.16 (m, 1H), 7.65 (t, 1H), 4.03 (d, 2H, J=5.8 Hz); MS: (+) m/z 382.19 (M+1).

Workup

  1. temperaturewas refluxed for 4 days before it
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in water (100 ml)
  4. extractionextracted with dichloromethane (3×50 ml)
  5. filtrationThe resulting precipitate was filtered
  6. washwashed with water
  7. customdried in vacuo

Sources & evidence

ORD record
ord-0eca64df285144868caa983bea63e539
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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