Methyl 2-chloro-4,4-dimethyl-3-oxopentanoate → Methyl 4-tert-butyl-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylate

HRID 2282182Notes

Reaction equation

HRID 2282182 reaction equation
Cl.[CH3:2][C:3]1[C:11]([C:12](=[S:14])[NH2:13])=[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][N:5]2[N:4]=1.Cl[CH:16]([C:21](=O)[C:22]([CH3:25])([CH3:24])[CH3:23])[C:17]([O:19][CH3:20])=[O:18]>CC(O)C>[C:22]([C:21]1[N:13]=[C:12]([C:11]2[C:3]([CH3:2])=[N:4][N:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=23)[S:14][C:16]=1[C:17]([O:19][CH3:20])=[O:18])([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 2

HCID 2779362Methyl 2-chloro-4,4-dimethyl-3-oxopentanoateHCID 866495852-Methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride

Product 1

HCID 66856383Methyl 4-tert-butyl-2-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,3-thiazole-5-carboxylateYield 77.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Using 2-methylpyrazolo[1,5-a]pyridine-3-carbothioamide hydrochloride (300 mg, 1.3 mmol) produced in Example 11-B(v), methyl 2-chloro-4,4-dimethyl-3-oxopentanoate (950 mg, 4.9 mmol) produced above and 2-propanol (25 mL) as starting materials and in the same manner as in Example 11-B (vi), the title compound (330 mg, 76%) was obtained as a yellow solid.

Sources & evidence

ORD record
ord-fa88b2c0bb634355a812b02268fccf0a
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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