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Hydrochloric Acid → 1-{5-[3-(Aminosulfonyl)phenyl]-6-(4-fluorophenyl)-2-(trifluoro methyl)pyrimidin-4-yl}piperidine-4-carboxylic acid

HRID 72681
Notes
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Reaction equation

HRID 72681 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[C:12]([N:28]3[CH2:33][CH2:32][CH:31]([C:34]([O:36]CC)=[O:35])[CH2:30][CH2:29]3)=[N:13][C:14]([C:24]([F:27])([F:26])[F:25])=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].O.[OH-].[Li+].Cl>O1CCCC1.O>[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[C:12]([N:28]3[CH2:33][CH2:32][CH:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]3)=[N:13][C:14]([C:24]([F:27])([F:25])[F:26])=[N:15][C:16]=2[C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:3])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 24959756Ethyl 1-{5-[3-(aminosulfonyl)phenyl]-6-(4-fluorophenyl)-2-(trifluoromethyl)pyrimidin-4-yl}piperidine-4-carboxylate

Product 1

HCID 249619571-{5-[3-(Aminosulfonyl)phenyl]-6-(4-fluorophenyl)-2-(trifluoro methyl)pyrimidin-4-yl}piperidine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 1-{5-[3-(aminosulfonyl)phenyl]-6-(4-fluorophenyl)-2-(trifluoromethyl)pyrimidin-4-yl}piperidine-4-carboxylate (0.4 g, 0.725 mmol) in tetrahydrofuran (4 ml) was treated with lithium hydroxide monohydrate (0.036 g, 0.87 mmol) in water (0.2 ml) and was stirred for 17 hours. Subsequently the reaction mixture was poured onto ice-cold water, acidified with dilute hydrochloric acid and extracted with dichloromethane (25 ml). Evaporation of organic layer furnished the required product. 1H-NMR (DMSO-d6) δ: 1.39 (m, 2H), 1.64 (m, 2H), 2.09 (m, 1H), 2.84-2.89 (m, 2H), 3.66 (m, 2H), 7.02-7.07 (m, 2H), 7.07-7.13 (m, 2H), 7.37-7.39 (m, 2H), 7.49-7.53 (m, 1H), 7.69 (s, 1H), 7.72-7.74 (d, 1H), 12.25 (br, 1H, D2O exchangeable); MS m/z: 525.0 (M++1).

Workup

  1. additionSubsequently the reaction mixture was poured onto ice-cold water
  2. extractionextracted with dichloromethane (25 ml)
  3. customEvaporation of organic layer

Sources & evidence

ORD record
ord-64206cb6d3f843b6b72707e934d3a52e
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08828999B2

Reaction notes

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