Trifluoroacetic acid → HCID 59232091, compound

HRID 1099301Notes

Reaction equation

HRID 1099301 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][N:35]=4)=[O:32])=[C:26]([F:44])[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:42])([F:43])[F:41])[CH:37]=[CH:36][N:35]=4)=[O:32])=[C:26]([F:44])[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 59231942HCID 59231942, compound

Product 1

HCID 59232091HCID 59232091, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of Example 270 (930 mg, 1.5 mmol) in 60 mL 1,2-dichloroethane was treated with 15 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 (705 mg, 91%) as a tan solid. 1H-NMR (DMSO-d6) δ 10.14 (bs, 1H), 10.06 (bs, 1H), 8.54 (d, 1H), 8.26 (t, 1H), 8.01 (s, 1H), 7.88 (s, 1H), 7.31-7.40 (m, 2H), 7.24 (dd, 1H), 6.65 (s, 1H), 3.18 (tt, 1H), 3.01 (broad d, 2H), 2.61 (td, 2H), 1.92 (broad d, 2H), 1.54 (ddd, 2H); MS [M+H]+=515.2; LCMS RT=2.34.

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-c05e400c4cba4920931b29f9dd0edbd1
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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