Trifluoroacetic acid → HCID 59232075, compound

HRID 1091483Notes

Reaction equation

HRID 1091483 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([NH:24]C(=O)OC(C)(C)C)=[C:20]([O:32][CH3:33])[CH:19]=3)[CH:9]=[C:10]([CH2:11][N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:24][C:21]1[CH:22]=[CH:23][C:18]([C:8]2[CH:9]=[C:10]([CH2:11][N:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[N:6]3[C:7]=2[C:2]([NH2:1])=[N:3][CH:4]=[N:5]3)=[CH:19][C:20]=1[O:32][CH3:33]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59231975HCID 59231975, compound

Product 1

HCID 59232075HCID 59232075, compoundYield 102.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of t-butyl {4-[4-amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]-2-methoxyphenyl}carbamate (100 mg, 0.22 mmol) in CH2Cl2 (4 ml) was added trifluoroacetic acid (1.5 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 and concentrated to afford 80 mg of the title compound. 1H-NMR (DMSO-d6) δ 7.84 (s, 1H), 6.84 (d, J=2 Hz, 1H), 6.84 to 6.68 (m, 2H), 6.55 (s, 1H), 4.87 (s, 2H), 4.01 to 3.99 (m, 5H), 3.53 (t, J=4 Hz, 4H), 2.42 (t, J=4 Hz, 4H).

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

Sources & evidence

ORD record
ord-cd5f6675664e4fb1abd888be636a4019
Source dataset
uspto-grants-2012_03
Patent number
US08129379B2

Reaction notes

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