2-(3,5-Dimethyl-1H-pyrazol-1-YL)-2-methylpropanoic acid → Ethyl 2-{1-[2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate

HRID 573244Notes

Reaction equation

HRID 573244 reaction equation
[Cl-].[CH2:2]([O:4][C:5]([C:7]1[N:8]=[C:9]([CH:12]2[CH2:17][CH2:16][NH2+:15][CH2:14][CH2:13]2)[S:10][CH:11]=1)=[O:6])[CH3:3].[CH3:18][C:19]1[CH:23]=[C:22]([CH3:24])[N:21]([C:25]([CH3:30])([CH3:29])[C:26](O)=[O:27])[N:20]=1>>[CH3:18][C:19]1[CH:23]=[C:22]([CH3:24])[N:21]([C:25]([CH3:30])([CH3:29])[C:26]([N:15]2[CH2:16][CH2:17][CH:12]([C:9]3[S:10][CH:11]=[C:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[N:8]=3)[CH2:13][CH2:14]2)=[O:27])[N:20]=1

Participants

3

Reactant 2

HCID 196185672-(3,5-Dimethyl-1H-pyrazol-1-YL)-2-methylpropanoic acidHCID 178470098HCID 178470098, compound

Product 1

HCID 66911550Ethyl 2-{1-[2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate

Procedure

4-[4-(Ethoxycarbonyl)-1,3-thiazol-2-yl]piperidinium chloride (VI-1, 8.23 g) is reacted analogously to Example IV-1 with 2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoic acid (5.42 g). This gives, after chromatographic purification, ethyl 2-{1-[2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate (9.64 g, 80%)

Workup

  1. customThis gives, after chromatographic purification, ethyl 2-{1-[2-(3,5-dimethyl-1H-pyrazol-1-yl)-2-methylpropanoyl]piperidin-4-yl}-1,3-thiazole-4-carboxylate (9.64 g, 80%)

Sources & evidence

ORD record
ord-6f739c00388541c6b9d73eb6099e2b9b
Source dataset
uspto-grants-2015_05
Patent number
US09029549B2

Reaction notes

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