Trifluoroacetic acid → HCID 44160138, compound

HRID 908376Notes

Reaction equation

HRID 908376 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([N:21]2[CH:25]=[C:24]([C:26]3[CH:27]=[N:28][C:29]([NH2:41])=[C:30]([C:32]4[S:33][C:34]5[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=5[N:36]=4)[CH:31]=3)[CH:23]=[N:22]2)[CH2:17][CH2:16]1)=O)(C)(C)C>ClCCl>[S:33]1[C:34]2[CH:40]=[CH:39][CH:38]=[CH:37][C:35]=2[N:36]=[C:32]1[C:30]1[C:29]([NH2:41])=[N:28][CH:27]=[C:26]([C:24]2[CH:23]=[N:22][N:21]([CH:18]3[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]3)[CH:25]=2)[CH:31]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57687053HCID 57687053, compound

Product 1

HCID 44160138HCID 44160138, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3 ml) was added to a stirred solution of tert-butyl-4-[4-[6-amino-5-(1,3-benzothiazol-2-yl)-3-pyridyl]pyrazol-1-yl]piperidine-1-carboxylate (0.300 g) in dichloromethane (4 ml). The mixture was stirred for 1 hour, then concentrated under reduced pressure. The residue was dissolved in DCM (60 ml) and the solution was washed with a 0.5M solution of aqueous sodium hydroxide (30 ml). The organic phases were washed with water (15 ml) and brine (15 ml). The aqueous phase was extracted with DCM (3×30 ml), and then the organic layers were combined and concentrated under reduced pressure. The residue was stirred in acetonitrile (10 ml) for 18 hours. The solid was filtered and dried under vacuum. There was thus obtained 3-(1,3-benzothiazol-2-yl)-5-[1-(4-piperidyl)pyrazol-4-yl]pyridin-2-amine (0.109 g); Mass Spectrum: M+H+ 377; NMR Spectrum: (DMSOd6 and CF3CO2D) 8.73 (d, 1H), 8.56 (d, 1H), 8.53 (s, 1H), 8.26 (d, 1H), 8.21 (d, 1H), 8.16 (s, 1H), 7.66 (dd, 1H), 7.59 (dd, 1H), 4.52-4.62 (m, 1H), 3.41-3.52 (m, 2H), 3.09-3.21 (m, 2H), 2.24-2.33 (m, 2H), 2.10-2.23 (m, 2H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in DCM (60 ml)
  3. washthe solution was washed with a 0.5M solution of aqueous sodium hydroxide (30 ml)
  4. washThe organic phases were washed with water (15 ml) and brine (15 ml)
  5. extractionThe aqueous phase was extracted with DCM (3×30 ml)
  6. concentrationconcentrated under reduced pressure
  7. stirringThe residue was stirred in acetonitrile (10 ml) for 18 hours
  8. filtrationThe solid was filtered
  9. customdried under vacuum

Sources & evidence

ORD record
ord-74396509eb534a5d9623d387716eaba6
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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