Trifluoroacetic acid → HCID 57955254, compound

HRID 1094865Notes

Reaction equation

HRID 1094865 reaction equation
[C:1]([C:4]1[C:5]([C:21]2[CH:26]=[CH:25][C:24]([NH:27]C(=O)OC(C)(C)C)=[C:23]([F:35])[CH:22]=2)=[C:6]2[N:11]([C:12]=1[CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)[N:10]=[CH:9][N:8]=[C:7]2[NH2:20])(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH2:20][C:7]1[C:6]2=[C:5]([C:21]3[CH:26]=[CH:25][C:24]([NH2:27])=[C:23]([F:35])[CH:22]=3)[C:4]([C:1](=[O:3])[CH3:2])=[C:12]([CH2:13][N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]2[N:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 57955241HCID 57955241, compound

Product 1

HCID 57955254HCID 57955254, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of CH2Cl2 (50 mL) was added of tert-butyl {4-[6-acetyl-4-amino-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-5-yl]-2 fluorophenyl}-carbamate (291 mg, 0.60 mmol) followed by trifluoroacetic acid (5 mL). The solution was allowed to stir for 30 min at rt. Aq saturated NaHCO3 was added to the solution until bubbling stopped. Additionally CH2Cl2 was added and the solution was then transferred to a separatory funnel. The organic layer was isolated while the aqueous layer was back extracted with CH2Cl2 (2×25 mL). The combined organic layers were collected, dried (MgSO4), filtered, and concentrated to dryness yielding 214 mg of the above compound as a white solid (0.56 mmol, yield 93%). 1H-NMR (DMSO-d6) δ 7.95 (s, 1H), 7.08 (dd, J=1.7 Hz, 10.3 Hz, 1H), 6.92 (dd, J=1.8 Hz, 7.9 Hz, 1H), 6.86 (t, J=8.7 Hz, 1H), 5.47 (s, 2H), 4.05 (s, 2H), 3.49 (m, 4H), 2.41 (m, 4H), 2.06 (s, 3H); MS [M+H]+=385.1; LCMS RT=1.16 min.

Workup

  1. customuntil bubbling
  2. additionAdditionally CH2Cl2 was added
  3. customthe solution was then transferred to a separatory funnel
  4. customThe organic layer was isolated while the aqueous layer
  5. extractionwas back extracted with CH2Cl2 (2×25 mL)
  6. customThe combined organic layers were collected
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-62a0f8eec5764648adfb28bbf0569894
Source dataset
uspto-grants-2012_03
Patent number
US08133995B2

Reaction notes

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