Hydrochloric Acid → HCID 178428307, compound

HRID 928147Notes

Reaction equation

HRID 928147 reaction equation
[F:1][CH2:2][C:3]([C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34]([O:36]CC)=[O:35])[CH2:30][CH2:29]1)([OH:27])[C:4]1[S:5][C:6]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:12]=[C:11]([CH3:26])[CH:10]=2)=[CH:7][N:8]=1.Cl>CS(C)=O>[F:1][CH2:2][C:3]([C@H:28]1[CH2:33][CH2:32][C@H:31]([C:34]([OH:36])=[O:35])[CH2:30][CH2:29]1)([OH:27])[C:4]1[S:5][C:6]([C:9]2[CH:14]=[C:13]([NH:15][C:16]3[N:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][N:17]=3)[CH:12]=[C:11]([CH3:26])[CH:10]=2)=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178472377HCID 178472377, compound

Product 1

HCID 178428307HCID 178428307, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Ethyl trans-4-{2-fluoro-1-hydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)-pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}cyclohexanecarboxylate (72 mg, 0.130 mmol) was dissolved in HCl (10 M in water, 2 ml, 20.0 mmol) and heated to reflux for 20 min. The reaction was diluted with DMSO and purified on reverse phase HPLC (acetonitrile/water with a 0.1% TFA modifier) to afford racemic trans-4-{2-fluoro-1-hydroxy-1-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)-1,3-thiazol-2-yl]ethyl}cyclohexanecarboxylic acid. MS ESI calc'd. for C24H24F4N4O3S [M+H]+ 525. found 525.

Workup

  1. temperatureheated
  2. temperatureto reflux for 20 min
  3. custompurified on reverse phase HPLC (acetonitrile/water with a 0.1% TFA modifier)

Sources & evidence

ORD record
ord-93491fc306284707b31733b7d3201c83
Source dataset
uspto-grants-2016_03
Patent number
US09290490B2

Reaction notes

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