Triethylamine → 1-[2-(1-Cyclobutyl-piperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]-propan-1-one

HRID 1402670Notes

Reaction equation

HRID 1402670 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][CH:8]([O:11][C:12]3[S:13][C:14]4[CH2:15][NH:16][CH2:17][CH2:18][C:19]=4[N:20]=3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:28](Cl)(=[O:31])[CH2:29][CH3:30]>ClCCl>[CH:1]1([N:5]2[CH2:6][CH2:7][CH:8]([O:11][C:12]3[S:13][C:14]4[CH2:15][N:16]([C:28](=[O:31])[CH2:29][CH3:30])[CH2:17][CH2:18][C:19]=4[N:20]=3)[CH2:9][CH2:10]2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 666146332-(1-Cyclobutyl-piperidin-4-yloxy)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine

Product 1

HCID 568490631-[2-(1-Cyclobutyl-piperidin-4-yloxy)-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl]-propan-1-oneYield 71.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-(1-Cyclobutyl-piperidin-4-yloxy)-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridine (1.3 grams, 4 mmol, obtained in above step) and triethylamine (1.9 mL, 13 mmol) in dichloromethane (30 mL) was cooled to 0° C. Propionylchloride (0.4 mL, 5 mmol) in dichloromethane (5 mL) was added drop wise over a period of 15 minutes and stirred the reaction for 30 minutes. Reaction mass was poured onto ice cold water and the product was extracted with ethyl acetate (3×50 mL). Combined organics were washed with water followed by brine and dried over anhydrous sodium sulphate. Organic volatiles were evaporated under vacuum. The residue was purified by flash chromatography (methanol/chloroform, 2/98) to obtain the title compound (1.0 gram).

Workup

  1. customthe reaction for 30 minutes
  2. customReaction mass
  3. additionwas poured onto ice cold water
  4. extractionthe product was extracted with ethyl acetate (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
  8. customThe residue was purified by flash chromatography (methanol/chloroform, 2/98)

Sources & evidence

ORD record
ord-326b92aba2d14b1e900519fdafae459f
Source dataset
uspto-grants-2014_12
Patent number
US08912179B2

Reaction notes

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