Hydrochloric Acid → HCID 67429444, compound

HRID 1040203Notes

Reaction equation

HRID 1040203 reaction equation
[CH3:1][C:2]1([CH3:36])[C:11]([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)([OH:12])[CH2:10][CH2:9][CH2:8][C:3]21OCC[O:4]2.Cl.C(=O)(O)[O-].[Na+]>C1COCC1>[OH:12][C:11]1([C:13]2[S:14][C:15]([C:18]3[CH:23]=[C:22]([NH:24][C:25]4[N:30]=[C:29]([C:31]([F:33])([F:34])[F:32])[CH:28]=[CH:27][N:26]=4)[CH:21]=[C:20]([CH3:35])[CH:19]=3)=[CH:16][N:17]=2)[CH2:10][CH2:9][CH2:8][C:3](=[O:4])[C:2]1([CH3:36])[CH3:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 67432981HCID 67432981, compound

Product 1

HCID 67429444HCID 67429444, compoundYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of the product of Step 1 (600 mg, 1.15 mmol) in THF (4 mL) was added HCl (6 M, 3.84 mL, 23.1 mmol). The reaction mixture was allowed to stir at room temperature for 30 min, neutralized with aqueous saturated sodium bicarbonate, and extracted with dichloromethane (3×). The combined organics were dried (sodium sulfate), filtered, concentrated, and purified by flash chromatography on silica to afford 3-hydroxy-2,2-dimethyl-3-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]cyclohexanone (534 mg, 1.12 mmol) as a yellow foam. MS ESI: [M+H]+ m/z 477.1.

Workup

  1. extractionextracted with dichloromethane (3×)
  2. dry with materialThe combined organics were dried (sodium sulfate)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-5c1a57609eb04f9ba7d8a2f44c7a8583
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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