Water → HCID 136376963, compound

HRID 2282252Notes

Reaction equation

HRID 2282252 reaction equation
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[C:17]([CH3:22])[C:18]([C:19](=[S:21])[NH2:20])=[C:12]2[CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH:24]([C:29](OC)=[O:30])[C:25]([O:27][CH3:28])=[O:26].O>CN(C=O)C>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[C:17]([CH3:22])[C:18]([C:19]3[S:21][C:24]([C:25]([O:27][CH3:28])=[O:26])=[C:29]([OH:30])[N:20]=3)=[C:12]2[CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 120070Dimethyl chloromalonateHCID 86649607HCID 86649607, compound

Product 1

HCID 136376963HCID 136376963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 5-(benzyloxy)-2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (3.45 g, 10.3 mmol) in DMF (100 mL), was added 94% dimethyl chloromalonate (2.79 mL, 20.6 mmol) and the mixture was stirred for 7.5 h at 100° C. The reaction mixture was allowed to cool to 50° C. and then was dropwise added water (100 mL). The resulting precipitate was collected by filtration and then washed with EtOH (20 mL) and diethyl ether (20 mL) to obtain methyl 2-[5-(benzyloxy)-2-methylpyrazolo[1,5-a]pyridin-3-yl]-4-hydroxy-1,3-thiazole-5-carboxylate as a orange solid, which was used in the next step without further purification. 1H-NMR (DMSO-d6, 300 MHz) 2.59 (3H, s), 3.75 (3H, s), 5.27 (2H, s), 6.87 (1H, dd, J=2.6, 7.6 Hz), 7.32-7.51 (3H, m), 7.52-7.64 (2H, m), 7.88 (1H, d, J=2.6 Hz), 8.67 (1H, d, J=7.6 Hz), 11.79 (1H, br s).

Workup

  1. temperatureto cool to 50° C.
  2. filtrationThe resulting precipitate was collected by filtration
  3. washwashed with EtOH (20 mL) and diethyl ether (20 mL)

Sources & evidence

ORD record
ord-f516fa7286b54102a94cd3a750d0f596
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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