Trifluoroacetic acid → HCID 67487773, compound

HRID 1809631Notes

Reaction equation

HRID 1809631 reaction equation
[CH3:1][O:2][CH2:3][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:23]12[NH:25][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH:18]([C:15]1[N:14]=[C:13]([NH:12][C:9]3[C:8]([O:33][C:34]4[C:35]([CH3:40])=[N:36][CH:37]=[CH:38][CH:39]=4)=[CH:7][C:6]([S:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:11][N:10]=3)[S:17][N:16]=1)[CH2:24]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71231959HCID 71231959, compound

Product 1

HCID 67487773HCID 67487773, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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) was dissolved in CH2Cl2 (4 mL) and TFA (2 mL) was added. The reaction was stirred at ambient temperature for 15 minutes. The reaction was concentrated and redissolved in CH2Cl2 and washed with saturated aqueous. NaHCO3, dried over sodium sulfate, filtered and concentrated to afford 3-(8-azabicyclo[3.2.1]octan-3-yl)-N-(5-(2-methoxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-yl)-1,2,4-thiadiazol-5-amine (193 mg, 0.398 mmol, 91.0% yield) as a crude yellow solid.

Workup

  1. concentrationThe reaction was concentrated
  2. dissolutionredissolved in CH2Cl2
  3. washwashed with saturated aqueous
  4. dry with materialNaHCO3, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ccdf660c6ac7474aa97f0bc55721797c
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

Loading…