Trifluoroacetic acid → 2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine

HRID 2387610Notes

Reaction equation

HRID 2387610 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][N:16](C(OC(C)(C)C)=O)[CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=[C:9]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[S:8]1)=[N+:2]=[N-:3].C(O)(C(F)(F)F)=O>C(Cl)Cl>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:11]([C:12]2[S:13][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:19]=3[N:20]=2)[N:10]=[C:9]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[S:8]1)=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86608771tert-butyl 2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate

Product 1

HCID 866087722-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridineYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of tert-butyl 2-(2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-6,7-dihydrothiazolo[5,4-c]pyridine-5(4H)-carboxylate (0.313 g, 0.524 mmol) in 10.0 mL of DCM at 0° C. was added TFA (1 mL). The mixture was stirred for 1 hour at 0° C. then at room temperature for 1 hour. The reaction was then concentrated to dryness and partitioned between EtOAc (30 mL) and saturated NaHCO3 solution (30 mL). The aqueous layer was extracted with EtOAc (2×20 mL) and the combined organic phases were washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo to afford the desired product as a yellow gum (0.251 g, 96%).

Workup

  1. waitat room temperature for 1 hour
  2. concentrationThe reaction was then concentrated to dryness
  3. custompartitioned between EtOAc (30 mL) and saturated NaHCO3 solution (30 mL)
  4. extractionThe aqueous layer was extracted with EtOAc (2×20 mL)
  5. washthe combined organic phases were washed with brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e5ded6ced0784da88020c47d41135f9f
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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