Trifluoroacetic acid → 2-(1-Cyclobutyl-piperidin-4-yloxy)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine

HRID 1402669Notes

Reaction equation

HRID 1402669 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]2[N:14]=[C:15]([O:17][CH:18]3[CH2:23][CH2:22][N:21]([CH:24]4[CH2:27][CH2:26][CH2:25]4)[CH2:20][CH2:19]3)[S:16][C:10]=2[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH:24]1([N:21]2[CH2:20][CH2:19][CH:18]([O:17][C:15]3[S:16][C:10]4[CH2:9][NH:8][CH2:13][CH2:12][C:11]=4[N:14]=3)[CH2:23][CH2:22]2)[CH2:25][CH2:26][CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 666112882-(1-Cyclobutyl-piperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester

Product 1

HCID 666146332-(1-Cyclobutyl-piperidin-4-yloxy)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridineYield 88.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(1-Cyclobutyl-piperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridine-5-carboxylic acid tert-butyl ester (2.0 grams, 5 mmol, obtained in above step) in dichloromethane (30 mL) was treated with trifluroacetic acid (5.0 mL, 50 mmol) at 0° C. Reaction mass was stirred for 4 hours. After completion of reaction, the reaction mass was quenched into ice cold water and adjust pH to 10, by using 40% aqueous sodium hydroxide solution. The product was extracted with dichloromethane (3×50 mL), combined organics were washed with water followed by brine and dried over anhydrous sodium sulphate. Organic volatiles were evaporated under vacuum to obtain the title compound (1.3 grams).

Workup

  1. customReaction mass
  2. customAfter completion of reaction
  3. customthe reaction mass was quenched into ice cold water
  4. extractionThe product was extracted with dichloromethane (3×50 mL)
  5. washcombined organics were washed with water
  6. dry with materialdried over anhydrous sodium sulphate
  7. customOrganic volatiles were evaporated under vacuum

Sources & evidence

ORD record
ord-eb1ee530168a44b3924490164f4f9968
Source dataset
uspto-grants-2014_12
Patent number
US08912179B2

Reaction notes

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