Hydrochloric Acid → HCID 44469184, compound

HRID 573247Notes

Reaction equation

HRID 573247 reaction equation
[F:1][CH:2]([F:30])[C:3]1[CH:7]=[C:6]([CH:8]([F:10])[F:9])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[S:21][CH:22]=[C:23]([C:25]([O:27]CC)=[O:26])[N:24]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1.Cl>O1CCCC1.O>[F:30][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([CH:8]([F:9])[F:10])[N:5]([CH2:11][C:12]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[S:21][CH:22]=[C:23]([C:25]([OH:27])=[O:26])[N:24]=3)[CH2:16][CH2:15]2)=[O:13])[N:4]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58242750HCID 58242750, compound

Product 1

HCID 44469184HCID 44469184, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylate (IV-1, 13.3 g) is dissolved in tetrahydrofuran (80 ml). LiOH monohydrate (1.86 g) dissolved in water (20 ml) is then added. After 3 hours, water is added, the pH is adjusted to 2-3 with dilute hydrochloric acid (1M), the mixture is then extracted with ethyl acetate and the combined organic phases are dried with sodium sulfate. The solid is filtered off and the solvent is removed by distillation. This gives 2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carboxylic acid (11.7 g, 94%).

Workup

  1. additionis then added
  2. extractionthe mixture is then extracted with ethyl acetate
  3. dry with materialthe combined organic phases are dried with sodium sulfate
  4. filtrationThe solid is filtered off
  5. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-2481ff2dc0e9426c8326d86f4df65891
Source dataset
uspto-grants-2015_05
Patent number
US09029549B2

Reaction notes

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