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Sodium hydride → 4-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-b]pyridine-2-yl)-amide

HRID 550836
Notes
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Reaction equation

HRID 550836 reaction equation
Cl[C:2]1[C:7]([NH:8][C:9]([NH:11][C:12]([N:14]2[CH2:19][CH2:18][C:17]([OH:30])([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[CH2:16][CH2:15]2)=[O:13])=[S:10])=[C:6]([O:31][CH3:32])[CH:5]=[CH:4][N:3]=1.[H-].[Na+].C(OCC)(=O)C.CCCCCC>C1COCC1>[CH3:32][O:31][C:6]1[CH:5]=[CH:4][N:3]=[C:2]2[S:10][C:9]([NH:11][C:12]([N:14]3[CH2:19][CH2:18][C:17]([OH:30])([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)[CH2:16][CH2:15]3)=[O:13])=[N:8][C:7]=12
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 21226206Ethyl acetate hexaneHCID 590119851-(2-Chloro-4-methoxy-pyridin-3-yl)-3-[4-hydroxy-4-(3-trifluoromethylphenyl)-piperidine-1-carbonyl]-thiourea

Product 1

HCID 248306154-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-b]pyridine-2-yl)-amideYield 22%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a magnetically stirred mixture of 1-(2-Chloro-4-methoxy-pyridin-3-yl)-3-[4-hydroxy-4-(3-trifluoromethylphenyl)-piperidine-1-carbonyl]-thiourea (100 mg, 0.20 mmol) in THF (10 mL) was added sodium hydride (10 mg, 0.25 mmole, 60% dispersion in mineral oil). The reaction is stirred at reflux overnight. TLC (80% ethyl acetate/hexane) indicated complete consumption of starting material. The reaction was poured into water and the aqueous layer was extracted with ethyl acetate. The resulting organic layers were washed with 2N HCl (2×) and saturated sodium chloride solution and then dried over magnesium sulfate. Purification by flash chromatography gave 4-Hydroxy-4-[3-(trifluoromethy)phenyl]piperidine-1-carboxylic acid (7-methoxy-thiazolo[5,4-b]pyridine-2-yl)-amide (20 mg, 0.04 mmole, 22% yield) as a light yellow solid. (LRMS for C20H19F3N4O3S (M+H)+ at m/z=452.

Workup

  1. temperatureat reflux overnight
  2. customconsumption of starting material
  3. additionThe reaction was poured into water
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe resulting organic layers were washed with 2N HCl (2×) and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customPurification by flash chromatography

Sources & evidence

ORD record
ord-00c1831b864f4f5a96cc85bcc69d66cb
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07947692B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes