Trifluoroacetic acid → HCID 11281098, compound

HRID 2216533Notes

Reaction equation

HRID 2216533 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:17]=[C:18](/[CH:20]=[CH:21]/[C:22]([O:24]C(C)(C)C)=[O:23])[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:16]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:17]=[C:18](/[CH:20]=[CH:21]/[C:22]([OH:24])=[O:23])[N:19]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 11442512HCID 11442512, compound

Product 1

HCID 11281098HCID 11281098, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 12.5 (53 mg, 0.116 mmol) in CH2Cl2 (2 ml) was added trifluoroacetic acid (3 ml) and the mixture was stirred for 17 h and concentrated. The crude product was purified by semi-preparative HPLC (gradient elution: 50 to 100% CH3CN/H2O+0.1% TFA) to afford 43 mg (72%) of 12.6. HRMS (ESI) calc'd for C25H27N2O3 403.2022, found 403.2026 (M+H+); 1H NMR (300 MHz, CDCl3) δ 7.59–7.56 (m, 3H), 7.46–7.34 (m, 6H), 7.13 (d, J=8.4, 2H), 6.74 (d, J=15.7, 1H), 5.12 (s, 2H), 4.20–4.11 (m, 1H), 2.07–2.03 (m, 2H), 1.95–1.89 (m, 2H), 1.75–1.71 (m, 3H), 1.28–1.25 (m, 3H).

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by semi-preparative HPLC (gradient elution: 50 to 100% CH3CN/H2O+0.1% TFA)

Sources & evidence

ORD record
ord-8728794284054670a92b14cd0bd161a4
Source dataset
uspto-grants-2006_09
Patent number
US07112601B2

Reaction notes

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