Trifluoroacetic acid → HCID 45789378, compound

HRID 2218959Notes

Reaction equation

HRID 2218959 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:10]=[C:11]([I:21])[C:12]2[O:16][C:15]([N:17]([CH3:19])[CH3:18])=[N:14][C:13]=2[CH:20]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:18][N:17]([CH3:19])[C:15]1[O:16][C:12]2[C:11]([I:21])=[CH:10][C:9]([CH2:8][NH2:7])=[CH:20][C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59770931HCID 59770931, compound

Product 1

HCID 45789378HCID 45789378, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Tert-butylN-{[2-(dimethylamino)-7-iodo-1,3-benzoxazol-5-yl]methyl}carbamate (120 mg, 0.29 mmol) in 4 ml of CH2Cl2 was added slowly 0.5 mL of trifluoroacetic acid and it was stirred at room temperature for 30 min. The excess of TFA was removed under vacuum. The product was purified by column chromatography (CH2Cl2/MeOH 9:1) yielding 64 mg (70%) of the title compound as a white solid. 1H NMR (CD3OD) δ 7.46 (d, 1H, J=1.5 Hz, H-6); 7.30 (d, 1H, J=1.5 Hz, H-4); 4.12 (s, 2H, CH2); 3.23, 3.24 (s, 6H, CH3×2); 13C NMR (CD3OD) δ 164.5 (C-2), 152.7 (C-7a), 144.6 (C-3a), 132.9 (C-5), 131.6 (C-6), 117.3 (C-4), 72.0 (C-7), 44.2 (CH2), 38.3 (CH3).

Workup

  1. customThe excess of TFA was removed under vacuum
  2. customThe product was purified by column chromatography (CH2Cl2/MeOH 9:1)

Sources & evidence

ORD record
ord-a16603914172476ca4f56842cc82a604
Source dataset
uspto-grants-2008_08
Patent number
US07414036B2

Reaction notes

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