Water → HCID 68707270, compound

HRID 1809615Notes

Reaction equation

HRID 1809615 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7]([C:11]2[N:15]=[C:14]([NH:16][C:17]3[N:22]=[CH:21][C:20]([S:23][CH2:24]CC(OC)=O)=[CH:19][C:18]=3[O:30][C:31]3[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=3)[S:13][N:12]=2)([CH3:10])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].CC(C)([O-])C.[K+].[C:44]([O:47][CH2:48]CBr)(=[O:46])[CH3:45].O>C1COCC1>[C:44]([O:47][CH2:48][CH2:24][S:23][C:20]1[CH:21]=[N:22][C:17]([NH:16][C:14]2[S:13][N:12]=[C:11]([C:7]3([CH3:10])[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]3)[N:15]=2)=[C:18]([O:30][C:31]2[C:32]([CH3:37])=[N:33][CH:34]=[CH:35][CH:36]=2)[CH:19]=1)(=[O:46])[CH3:45]

Participants

6

Reactant 4

HCID 962WaterHCID 135641-Acetoxy-2-bromoethaneHCID 23665647Potassium tert-butoxideHCID 68709795HCID 68709795, compound

Product 1

HCID 68707270HCID 68707270, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(6-(3-(1-acetyl-4-methylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)propanoate (125 mg, 0.230 mmol) was dissolved in THF (10 mL) and potassium tert-butoxide (64.6 mg, 0.576 mmol) was added. The reaction was stirred for 30 seconds and 2-bromoethyl acetate (38.5 mg, 0.230 mmol) was added. The reaction was stirred for 3 hours. Water was added and the reaction was extracted with dichloromethane. The organic layer was concentrated, and the crude material was purified by silica gel chromatography (5-7% methanol in dichloromethane) to give 2-(6-(3-(1-acetyl-4-methylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)ethyl acetate (89 mg, 0.164 mmol, 71.2% yield).

Workup

  1. stirringThe reaction was stirred for 3 hours
  2. extractionthe reaction was extracted with dichloromethane
  3. concentrationThe organic layer was concentrated
  4. customthe crude material was purified by silica gel chromatography (5-7% methanol in dichloromethane)

Sources & evidence

ORD record
ord-6f0cc8c308f84c7eb7601a8bbd8ebd66
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…