Acetic Acid → HCID 67458884, compound

HRID 554859Notes

Reaction equation

HRID 554859 reaction equation
[NH:1]1[CH2:4][CH:3]([O:5][C:6]2[CH:11]=[CH:10][C:9]([N:12]3[CH:17]=[CH:16][C:15]4[N:18]=[C:19]([C:21]5[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=5)[S:20][C:14]=4[C:13]3=[O:31])=[CH:8][C:7]=2[O:32][CH3:33])[CH2:2]1.[C:34]1(=O)[CH2:37][CH2:36][CH2:35]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.C(=O)(O)[O-].[Na+]>ClC(Cl)C>[CH:34]1([N:1]2[CH2:4][CH:3]([O:5][C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]5[N:18]=[C:19]([C:21]6[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:28])[F:30])=[CH:25][CH:26]=6)[S:20][C:14]=5[C:13]4=[O:31])=[CH:8][C:7]=3[O:32][CH3:33])[CH2:2]2)[CH2:37][CH2:36][CH2:35]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 14496CyclobutanoneHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 67459150HCID 67459150, compound

Product 1

HCID 67458884HCID 67458884, compoundYield 39.5%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Dissolve 5-[4-(azetidin-3-yloxy)-3-methoxy-phenyl]-2-(4-trifluoromethyl-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one (0.909 g, 1.92 mmol) in dichloroethane (25 mL) and add cyclobutanone (0.502 mL, 6.72 mmol), sodium triacetoxyborohydride (0.814 g, 3.84 mmol), and acetic acid (0.22 mL, 3.84 mmol). Stir the mixture overnight, add saturated sodium bicarbonate, and extract with dichloromethane (3×). Dry the mixture using sodium sulfate, filter, and concentrate. Purify via silica gel chromatography using a 0-4.5% gradient of 2N ammonia in methanol/dichloromethane to give 0.400 g (39%) of the desired product. MS/ES m/z 528.0 [M+1]+.

Workup

  1. extractionextract with dichloromethane (3×)
  2. customDry the mixture
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify via silica gel chromatography

Sources & evidence

ORD record
ord-42ce11089a6e4679944a9c73c4a5ebdd
Source dataset
uspto-grants-2011_11
Patent number
US08049013B2

Reaction notes

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