Trifluoroacetic acid → HCID 60198785, compound

HRID 2279579Notes

Reaction equation

HRID 2279579 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:20][C:21]([N:23]2[CH2:32][CH2:31][C:30]3[CH:29]=[N:28][C:27]([NH:33][CH:34]([CH3:36])[CH3:35])=[N:26][C:25]=3[CH2:24]2)=[O:22])[CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)[CH:5]=[CH:6][C:7]=1[Cl:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:12][CH2:11][CH2:10][CH:9]([NH:20][C:21]([N:23]1[CH2:32][CH2:31][C:30]2[CH:29]=[N:28][C:27]([NH:33][CH:34]([CH3:36])[CH3:35])=[N:26][C:25]=2[CH2:24]1)=[O:22])[C:4]1[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68295331HCID 68295331, compound

Product 1

HCID 60198785HCID 60198785, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 300 (29 mg, 0.0540 mmol) in DCM (2 mL) was added TFA (1 mL, 13.0 mmol). The reaction was stirred at RT 30 min, concentrated, and partitioned between DCM (15 mL) and satd. aq. NaHCO3 (15 mL). The phases were separated and the aqueous phase extracted with DCM (15 mL). The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified on a preparative SiO2 TLC plate (0.5 mm) developed with MeOH/DCM/NH4OH (9/90/1) to afford 11 mg (47%) of I-110 as a colorless glass: 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.63 (br s, 1H), 7.39 (d, 1H), 7.36 (d, J=8.2 Hz, 1H), 7.15 (dd, 1H), 4.97 (m, 1H), 4.83 (d, 1H), 4.38 (m, 2H), 4.10 (m, 1H), 3.70 (m, 1H), 3.60 (m, 1H), 2.89 (br s, 2H), 2.64 (t, 2H) 1.97 (m, 1H), 1.81 (m, 1H), 1.21 (d, 6H); LRMS (APCI pos) m/e=437.1 (M+H).

Workup

  1. concentrationconcentrated
  2. custompartitioned between DCM (15 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase extracted with DCM (15 mL)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified on a preparative SiO2 TLC plate (0.5 mm)
  9. customto afford 11 mg (47%) of I-110 as a colorless glass

Sources & evidence

ORD record
ord-f841e4c4f1cb4a4d80e6f9d6654cbf2d
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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