Trifluoroacetic acid → HCID 25212744, compound

HRID 2196541Notes

Reaction equation

HRID 2196541 reaction equation
[CH3:1][O:2][C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[N:13]([C@@H:14]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21](C)[C:22](=O)OC(C)(C)C)[CH2:15]2)[N:12]=[C:11]([C:30]([F:33])([F:32])[F:31])[CH:10]=1)=[O:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:37]=[CH:36][CH:35]=[CH:34][C:4]=1[CH2:5][NH:6][C:7]([C:9]1[N:13]([C@@H:14]2[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][NH:21][CH3:22])[CH2:15]2)[N:12]=[C:11]([C:30]([F:31])([F:32])[F:33])[CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59843246HCID 59843246, compound

Product 1

HCID 25212744HCID 25212744, compoundYield 123.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 77 (10 mg, 0.019 mmol) in CH2Cl2 (0.38 mL) was added TFA (0.073 mL, 0.951 mmol). The resulting solution was allowed to stir at room temperature for 2 h. The mixture was concentrated and the residue was purified by silica gel column chromatography with gradient of methanol (5-30%) in dichloromethane to afford 78 (10 mg, 80%) as a white solid. 1H NMR (DMSO-d6) δ(ppm): 9.11 (t, J=5.1 Hz, 1H), 7.38 (s, 1H), 7.27-7.19 (m, 2H), 7.00 (d, J=7.8 Hz, 1H), 6.91 (t, J=7.4 Hz, 1H), 5.83 (qi, J=9.0 Hz, 1H), 4.41 (q, J=6.1 Hz, 2H), 3.81 (s, 3H), 3.20-3.16 (m, 1H), 2.96-2.92 (m, 2H), 2.80-2.68 (m, 4H), 2.53 (d, J=2.2 Hz, 3H), 2.32-2.17 (m, 3H). LRMS (ESI): calc. 425.2; found 426.1 (MH)+.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by silica gel column chromatography with gradient of methanol (5-30%) in dichloromethane

Sources & evidence

ORD record
ord-b278d053e0384fc5976ad96e184c2ad2
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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