Trifluoroacetic acid → HCID 67486978, compound

HRID 1809625Notes

Reaction equation

HRID 1809625 reaction equation
[CH3:1][O:2][C:3](=[O:41])[CH2:4][S:5][C:6]1[CH:7]=[C:8]([O:33][C:34]2[C:35]([CH3:40])=[N:36][CH:37]=[CH:38][CH:39]=2)[C:9]([NH:12][C:13]2[S:17][N:16]=[C:15]([CH:18]3[CH2:24][CH:23]4[N:25](C(OC(C)(C)C)=O)[CH:20]([CH2:21][CH2:22]4)[CH2:19]3)[N:14]=2)=[N:10][CH:11]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:20]12[NH:25][CH:23]([CH2:22][CH2:21]1)[CH2:24][CH:18]([C:15]1[N:14]=[C:13]([NH:12][C:9]3[N:10]=[CH:11][C:6]([S:5][CH2:4][C:3]([O:2][CH3:1])=[O:41])=[CH:7][C:8]=3[O:33][C:34]3[C:35]([CH3:40])=[N:36][CH:37]=[CH:38][CH:39]=3)[S:17][N:16]=1)[CH2:19]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68705417HCID 68705417, compound

Product 1

HCID 67486978HCID 67486978, compoundYield 105%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(5-(5-(2-methoxy-2-oxoethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (461 mg, 0.770 mmol) was dissolved in CH2Cl2 (10 mL) and TFA (5 mL) was added. The reaction was stirred at ambient temperature for 15 minutes. The reaction was partitioned between CH2Cl2 and saturated aqueous NaHCO3, dried over sodium sulfate, filtered and concentrated to afford methyl 2-(6-(3-(8-azabicyclo[3.2.1]octan-3-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)acetate (402 mg, 0.806 mmol, 105% yield) as a pale yellow foam.

Workup

  1. customThe reaction was partitioned between CH2Cl2 and saturated aqueous NaHCO3
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e614a61f95ea44bd8c2e19def66a5adf
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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