Potassium Hydroxide → 2-(3-((5-Cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclohexyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylic acid

HRID 1748209Notes

Reaction equation

HRID 1748209 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C@@H:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]3[C:15]([F:18])([F:17])[F:16])[C:5]=2[CH2:19][O:20][CH:21]2[CH2:27][CH:26]3[N:28]([C:29]4[S:30][C:31]5[CH:37]=[C:36]([C:38]([O:40]CC)=[O:39])[CH:35]=[CH:34][C:32]=5[N:33]=4)[CH:23]([CH2:24][CH2:25]3)[CH2:22]2)[CH2:3][CH2:2]1.[OH-].[K+]>C(O)C>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C@@H:9]3[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]3[C:15]([F:17])([F:16])[F:18])[C:5]=2[CH2:19][O:20][CH:21]2[CH2:22][CH:23]3[N:28]([C:29]4[S:30][C:31]5[CH:37]=[C:36]([C:38]([OH:40])=[O:39])[CH:35]=[CH:34][C:32]=5[N:33]=4)[CH:26]([CH2:25][CH2:24]3)[CH2:27]2)[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 59054384Ethyl 2-(3-((5-cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclohexyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate

Product 1

HCID 867044122-(3-((5-Cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclohexyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylic acid

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of ethyl 2-(3-((5-cyclopropyl-3-((trans)-2-(trifluoromethyl)cyclohexyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)benzo[d]thiazole-6-carboxylate (16 mg, 0.03 mmol) in ethanol (1 mL) was treated with potassium hydroxide (4.5 mg, 0.08 mmol) and heated to 60° C. for 2 hours. The reaction cooled RT, was concentrated in vacuo and then treated with 10% citric acid (aq.) and extracted with EtOAc. Organics were collected and concentrated. The crude material was purified via mass-directed reverse phase HPLC.

Workup

  1. temperatureThe reaction cooled RT
  2. concentrationwas concentrated in vacuo
  3. additiontreated with 10% citric acid (aq.)
  4. extractionextracted with EtOAc
  5. customOrganics were collected
  6. concentrationconcentrated
  7. customThe crude material was purified via mass-directed reverse phase HPLC

Sources & evidence

ORD record
ord-2876fea3bcbd4e298211c78942b94f15
Source dataset
uspto-grants-2015_10
Patent number
US09150568B2

Reaction notes

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