Trifluoroacetic acid → HCID 59232012, compound

HRID 1099300Notes

Reaction equation

HRID 1099300 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[C:38]([C:40]([F:43])([F:42])[F:41])[CH:37]=[CH:36][C:35]=4[F:44])=[O:32])=[C:26]([Cl:45])[CH:25]=3)[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O.C(OCC)(=O)C>ClCCCl>[NH2:1][C:2]1[C:7]2=[C:8]([C:24]3[CH:29]=[CH:28][C:27]([NH:30][C:31]([NH:33][C:34]4[CH:39]=[C:38]([C:40]([F:43])([F:41])[F:42])[CH:37]=[CH:36][C:35]=4[F:44])=[O:32])=[C:26]([Cl:45])[CH:25]=3)[CH:9]=[C:10]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 8857Ethyl AcetateHCID 59231928HCID 59231928, compound

Product 1

HCID 59232012HCID 59232012, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of Example 266 (1.64 g, 2.53 mmol) in 50 mL 1,2-dichloroethane was treated with 10 mL TFA at rt. The reaction quickly became homogeneous and at 10 min no starting material remained by RP-HPLC. The reaction mixture was concentrated in vacuo, and the residue taken up again in fresh 1,2-dichloroethane and concentrated again; this was repeated 2 times. The residue was taken up in THF (15 mL) and EtOAc (85 mL) and washed with aq. sodium carbonate. The organic layer was dried with sodium sulfate and concentrated in vacuo to provide a tan solid. Trituration with ethyl acetate provided the title compound (1.2 g, 87%) as a tan solid. 1H-NMR (DMSO-d6) δ 8.64 (dd, 1H), 8.23 (d, 1H), 7.88 (s, 1H), 7.46-7.54 (m, 2H), 7.34-7.43 (m, 2H), 6.55 (s, 1H), 3.17 (tt, 2H), 2.96-3.05 (m, 2H), 2.60 (dd, 2H), 1.60-1.85-1.95 (m, 2H), 1.56 (ddd, 2H); MS [M+H]+=548.3; LCMS RT=2.94 min.

Workup

  1. customThe reaction quickly became homogeneous
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. concentrationconcentrated again
  4. washEtOAc (85 mL) and washed with aq. sodium carbonate
  5. dry with materialThe organic layer was dried with sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customto provide a tan solid

Sources & evidence

ORD record
ord-672540e72bca4a8db09ce2ba1858ea40
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

Loading…