Trifluoroacetic acid → HCID 59231991, compound

HRID 1972763Notes

Reaction equation

HRID 1972763 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8](C3C=CC4C(C=3)=NN(CC3C=CC=CC=3)C=4)[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>ClCCl>[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 58529649HCID 58529649, compound

Product 1

HCID 59231991HCID 59231991, compoundYield 152.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[4-amino-5-(2-benzyl-2H-indazol-6-yl)pyrrolo[2,1-f][1,2,4]triazin-7-yl]piperidine-1-carboxylate (325 mg, 0.62 mmol) in dichloromethane (3 mL) was added trifluoroacetic acid (1 mL). The reaction was stirred (rt) for 17 h. The mixture was made basic (pH 9) with the addition of saturated aqueous NaHCO3 and the layers were separated. The aqueous phase was back extracted with dichloromethane (2×10 mL) and the combined organics were washed with brine, dried (Na2SO4), and evaporated to afford 299 mg (100%) of the desired product, which contained trace impurities. 1H NMR (300 MHz, DMSO-d6) δ 8.53 (s, 1 H), 7.87 (s, 1 H), 7.78 (d, 1 H), 7.57 (s, 1 H), 7.36-7.30 (m, 5 H), 7.13 (d, 1 H), 6.55 (s, 1 H), 5.64 (s, 2 H), 3.41 (br s, 1 H), 3.30-3.18 (m, 1 H), 3.07 (d, 2 H), 2.75-2.64 (m, 2H), 1.97 (d, 2 H), 1.68-1.53 (m, 2 H); ES-MS m/z 424.3 [M+H]+, HPLC RT (min) 0.78.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous phase was back extracted with dichloromethane (2×10 mL)
  3. washthe combined organics were washed with brine
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-0d095469ecc545139497bfb223a487e6
Source dataset
uspto-grants-2013_04
Patent number
US08431695B2

Reaction notes

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