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

HRID 1966348Notes

Reaction equation

HRID 1966348 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]

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 962WaterSolventHCID 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-81df0c74f1444d71860082227b5a2780
Source dataset
uspto-grants-2013_04
Patent number
US08420653B2

Reaction notes

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