2-Bromoethyl methyl ether → HCID 71231959, compound

HRID 1809630Notes

Reaction equation

HRID 1809630 reaction equation
COC(=O)[CH2:4][CH2:5][S:6][C:7]1[CH:8]=[C:9]([O:34][C:35]2[C:36]([CH3:41])=[N:37][CH:38]=[CH:39][CH:40]=2)[C:10]([NH:13][C:14]2[S:18][N:17]=[C:16]([CH:19]3[CH2:25][CH:24]4[N:26]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH:21]([CH2:22][CH2:23]4)[CH2:20]3)[N:15]=2)=[N:11][CH:12]=1.C[C:44]([O-:47])(C)C.[K+].BrCCOC>C1COCC1>[CH3:44][O:47][CH2:4][CH2:5][S:6][C:7]1[CH:8]=[C:9]([O:34][C:35]2[C:36]([CH3:41])=[N:37][CH:38]=[CH:39][CH:40]=2)[C:10]([NH:13][C:14]2[S:18][N:17]=[C:16]([CH:19]3[CH2:20][CH:21]4[N:26]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[CH:24]([CH2:23][CH2:22]4)[CH2:25]3)[N:15]=2)=[N:11][CH:12]=1

Participants

5

Reactant 3

HCID 809722-Bromoethyl methyl etherHCID 23665647Potassium tert-butoxideHCID 68710342HCID 68710342, compound

Product 1

HCID 71231959HCID 71231959, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-(5-(5-(3-methoxy-3-oxopropylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (347 mg, 0.566 mmol) was dissolved in THF (5 mL) and potassium 2-methylpropan-2-olate (1699 μL, 1.70 mmol) was added. The reaction was stirred for 5 minutes. 1-Bromo-2-methoxyethane (53.2 μL, 0.566 mmol) was added and the reaction was stirred at ambient temperature for 1 hour. The reaction was partitioned between saturated aqueous NH4Cl and CH2Cl2, dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel (100% EtOAc) to afford tert-butyl 3-(5-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (256 mg, 0.438 mmol, 77.3% yield) as a white solid.

Workup

  1. stirringthe reaction was stirred at ambient temperature for 1 hour
  2. customThe reaction was partitioned between saturated aqueous NH4Cl and CH2Cl2
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on silica gel (100% EtOAc)

Sources & evidence

ORD record
ord-a31a6135746b429bafbb0a9d4f9a6ed8
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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