Trifluoroacetic acid → 3-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amine

HRID 2387629Notes

Reaction equation

HRID 2387629 reaction equation
N1C2CCNCC=2SC=1.[N:10]([CH2:13][CH2:14][CH2:15][C:16]1([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:20]([C:21]2[S:22][C:23]3[CH2:24][N:25]([C:30](OC(C)(C)C)=O)[CH2:26][CH2:27][C:28]=3[N:29]=2)[N:19]=[C:18]([C:37]2[CH:42]=[C:41]([F:43])[CH:40]=[CH:39][C:38]=2[F:44])[S:17]1)=[N+]=[N-].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:44][C:38]1[CH:39]=[CH:40][C:41]([F:43])=[CH:42][C:37]=1[C:18]1[S:17][C:16]([CH2:15][CH2:14][CH2:13][NH2:10])([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[N:20]([C:21]2[S:22][C:23]3[CH2:24][N:25]([CH3:30])[CH2:26][CH2:27][C:28]=3[N:29]=2)[N:19]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 219419924H,5H,6H,7H-(1,3)thiazolo(5,4-c)pyridineHCID 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 119599503-(5-(2,5-Difluorophenyl)-3-(5-methyl-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propan-1-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Preparation of 24243-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazol-3(2H)-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridine: 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 mixture was then concentrated to dryness and partitioned between EtOAc (30 mL) and a 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 mixture was then concentrated to dryness
  3. custompartitioned between EtOAc (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-130a8523a9e745e69277e6e16e815b3a
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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