Trifluoroacetic acid → HCID 59231992, compound

HRID 1091482Notes

Reaction equation

HRID 1091482 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[N:19]3[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([NH:27]C(=O)OC(C)(C)C)=[C:23]([F:35])[CH:22]=3)[CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O.C(Cl)Cl.CO>C(Cl)Cl>[C:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]2[N:19]3[C:14]([C:15]([NH2:20])=[N:16][CH:17]=[N:18]3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([F:35])[CH:22]=3)[CH:12]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226129Dichloromethane methanolHCID 59232204HCID 59232204, compound

Product 1

HCID 59231992HCID 59231992, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl (4-{7-[(4-acetylpiperazin-1-yl)methyl]-4-aminopyrrolo[2,1-f][1,2,4]triazin-5-yl}-2-fluorophenyl)carbamate (320 mg, 0.62 mmol) in CH2Cl2 (8 ml) was added TFA (3 ml) and was stirred at rt for 3 h. The reaction mixture was partially evaporated and was added 10 ml ethyl acetate and washed with saturated aq. NaHCO3. The organic was dried over Na2SO4, concentrated and purified via column chromatography (95:5, v/v, CH2Cl2-CH3OH) to afford 74 mg of the title compound (yield 30%). 1H-NMR (CH3OH-d4) δ 7.85 (s, 1H), 7.10 to 7.00 (m, 3H), 6.66 (s, 1H), 4.00 (s, 2H), 3.60 to 3.50 (m, 4H), 2.63 to 2.55 (m, 4H), 20.6 (s, 3H); MS [M+H]+=383.9; LCMS RT=1.10 min.

Workup

  1. customThe reaction mixture was partially evaporated
  2. additionwas added 10 ml ethyl acetate
  3. washwashed with saturated aq. NaHCO3
  4. dry with materialThe organic was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified via column chromatography (95:5

Sources & evidence

ORD record
ord-fdf2f59e71d8424f87f97aba43ad1202
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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