Trifluoroacetic acid → HCID 11548026, compound

HRID 221906Notes

Reaction equation

HRID 221906 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9](=[O:44])[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]4[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=4)=[CH:29][CH:28]=3)=[O:25])=[CH:21][C:20]([C:40]([CH3:43])([CH3:42])[CH3:41])=[N:19]2)=[CH:14][CH:13]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C1COCC1>[NH2:7][CH2:8][C:9]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([NH:23][C:24]([NH:26][C:27]3[CH:32]=[CH:31][C:30]([O:33][C:34]4[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=4)=[CH:29][CH:28]=3)=[O:25])=[CH:21][C:20]([C:40]([CH3:43])([CH3:42])[CH3:41])=[N:19]2)=[CH:14][CH:13]=1)=[O:44]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59557927HCID 59557927, compound

Product 1

HCID 11548026HCID 11548026, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {[4-(3-tert-butyl-5-{3-[4-(pyridin-4-yloxy)-phenyl]-ureido}-pyrazol-1-yl)-benzylcarbamoyl]-methyl}-carbamic acid tert-butyl ester (60 mg, 0.10 mmol) in THF (5 mL) was added TFA (3 mL), and the resulting mixture was stirred at room temperature for 18 h. The reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 aqueous solution (20 mL), and the organic layer was removed and washed with brine, dried over Na2SO4, and concentrated at reduced pressure. The residue was purified by preparative TLC (90:10 CH2Cl2/MeOH) to give 10 mg (20%) of the desired product. 1H-NMR (DMSO-d6) δ 8.72 (s, 1H), 8.32 (d, J=5.7 Hz, 2H), 8.02 (s, 1H), 7.53 to 7.30 (m, 6H), 6.96 (d, J=6.6 Hz, 2H), 6.73 (d, J=6.3 Hz, 2H), 6.32 (s, 1H), 4.36 (s, 2H), 3.70 (S, 2H), 1.18 (s, 9H); MS LC-MS [M+H]+=513, RT=2.01 min.

Workup

  1. customThe reaction mixture was partitioned between EtOAc (20 mL) and saturated NaHCO3 aqueous solution (20 mL)
  2. customthe organic layer was removed
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated at reduced pressure
  6. customThe residue was purified by preparative TLC (90:10 CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-1a14deba7ed44c8e8adb779ae0ff4f1f
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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