Trifluoroacetic acid → HCID 59231994, compound

HRID 1099273Notes

Reaction equation

HRID 1099273 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([NH:24]C(OC(C)(C)C)=O)=[CH:20][CH:19]=3)[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O>ClCCl>[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[CH:9]=[C:10]([C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59232085HCID 59232085, compound

Product 1

HCID 59231994HCID 59231994, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of butyl 4-amino-5-{4-[(tert-butoxycarbonyl)amino]phenyl}pyrrolo[2,1-f][1,2,4]triazine-7-carboxylate (174.5 mg, 0.41 mmol) in dichloromethane (4 mL) was added TFA (2 mL). The solution was stirred at rt for 6.5 h and then the volatiles were evaporated under reduced pressure. The residue was dissolved in ethyl acetate (150 mL) and then this solution was washed with saturated aqueous sodium bicarbonate solution and water, dried over sodium sulfate, and concentrated to dryness under reduced pressure to afford 132.7 mg (99%) of the title compound. 1H-NMR (DMSO-d6) δ 8.10 (bs, 1 H), 8.02 (s, 1 H), 7.10 (d, J=8.3 Hz, 2 H), 7.08 (s, 1 H), 6.64 (d, J=8.4 Hz, 2 H), 5.55 (bs, 1 H), 5.34 (s, 2 H), 4.24 (t, J=6.5 Hz, 2 H), 1.70-1.63 (m, 2 H), 1.46-1.37 (m, 2 H), 0.93 (t, J=7.4, 3 H); MS [M+H]+=326.3; LCMS RT=2.07 min.

Workup

  1. customthe volatiles were evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (150 mL)
  3. washthis solution was washed with saturated aqueous sodium bicarbonate solution and water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-83ce445aafec47fa9a84ee0f059377ff
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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