Trifluoroacetic acid → HCID 67487214, compound

HRID 1809622Notes

Reaction equation

HRID 1809622 reaction equation
[CH3:1][C:2]1[C:7]([O:8][C:9]2[C:10]([NH:22][C:23]3[S:27][N:26]=[C:25]([CH:28]4[CH2:34][CH:33]5[N:35](C(OC(C)(C)C)=O)[CH:30]([CH2:31][CH2:32]5)[CH2:29]4)[N:24]=3)=[N:11][CH:12]=[C:13]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH:14]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH:30]12[NH:35][CH:33]([CH2:32][CH2:31]1)[CH2:34][CH:28]([C:25]1[N:24]=[C:23]([NH:22][C:10]3[C:9]([O:8][C:7]4[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=4)=[CH:14][C:13]([S:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=4)=[CH:12][N:11]=3)[S:27][N:26]=1)[CH2:29]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68710136HCID 68710136, compound

Product 1

HCID 67487214HCID 67487214, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(5-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-8-azabicyclo[3.2.1]octane-8-carboxylate (550 mg, 0.911 mmol) was dissolved in CH2Cl2 (2 mL) and TFA (1 mL) was added and the reaction was stirred for 45 minutes. The reaction was partitioned between saturated aqueous NaHCO3 and CH2Cl2, dried over sodium sulfate, filtered and concentrated to afford 3-(8-azabicyclo[3.2.1]octan-3-yl)-N-(3-(2-methylpyridin-3-yloxy)-5-(pyridin-2-ylthio)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (438 mg, 0.870 mmol, 95.5% yield).

Workup

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

Sources & evidence

ORD record
ord-7e0333a17ea5437c987c6283dd4caacb
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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