Glycine → HCID 68426652, compound
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]([C:21]#[N:22])=[CH:17][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>>[C:21]([C:18]1[CH:19]=[CH:20][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:16][CH:17]=1)#[N:22]Participants
Procedure
A mixture of 2-(4-cyano-phenyl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (111 mg, 0.34 mmole) and glycine (512 mg, 6.82 mmole) in 0.5 M sodium methoxide/methanol (13 ml, 6.48 mmole) was refluxed for 45 h before it was cooled to room temperature and concentrated in vacuo. The residue was dissolved in water (35 ml) and extracted with methyl tert-butyl ether (2×25 ml). The remaining aqueous layer was acidified to pH=3 with 1N HCl (9 ml). The suspension was extracted with chloroform/isopropanol (3:1, 35 ml). The organic suspension was concentrated, washed with water and dried in vacuo to give the title compound as a brown solid (52 mg). 1H NMR (DMSO-d6, 200 MHz): δ=9.52 (t, 1H), 8.90 (s, 1H), 8.30 (d, 1H, J=8.2 Hz), 8.04 (d, 1H, J=8.2 Hz), 4.00 (d, 2H, J=5.8 Hz); MS: (+) m/z 355.22 (M+1).
Workup
- temperaturewas refluxed for 45 h before it
- concentrationconcentrated in vacuo
- dissolutionThe residue was dissolved in water (35 ml)
- extractionextracted with methyl tert-butyl ether (2×25 ml)
- extractionThe suspension was extracted with chloroform/isopropanol (3:1, 35 ml)
- concentrationThe organic suspension was concentrated
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-d98b093c7e214d4cb7c0c20dacc07e34
- Source dataset
- uspto-grants-2010_04
- Patent number
- US07696223B2
Reaction notes
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