HCID 69270451, compound → HCID 69270495, compound

HRID 2221115Notes

Reaction equation

HRID 2221115 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:10]([N+:25]([O-:27])=[O:26])[CH:9]=1)(C)(C)C>C(Cl)Cl>[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:24])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[C:10]([N+:25]([O-:27])=[O:26])[CH:9]=1

Participants

3

Reactant 1

HCID 69270451HCID 69270451, compound

Product 1

HCID 69270495HCID 69270495, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred suspension of {4-[2-(4-fluorophenyl)-acetylamino]-3-nitro-phenyl}-carbamic acid tert-butyl ester (2.40 g, 6.16 mmol) in methylene chloride (5 mL) trifluoroacetic acid (5 mL) was added. After 15 minutes methylene chloride was distilled off and the residual solution was transferred into saturated aqueous NaHCO3 solution (200 mL) with sonication. The precipitate was filtered, washed with water and dried in vacuo to furnish 1.70 g of the title compound as a red-brown solid. Yield 96.3%. LC/MS; tR=2.25 (UV, ELSD) 89%, 100%. 1H NMR (DMSO-d6): 3.59 (s, 2H); 5.65 (b, 2H, NH2); 6.83 (dd, 1H); 7.08 (d, 1H); 7.15 (t, 2H), 7.21 (d, 1H); 7.32 (dd, 2H); 9.91 (s, 1H, NH).

Workup

  1. additionwas added
  2. distillationAfter 15 minutes methylene chloride was distilled off
  3. customthe residual solution was transferred into saturated aqueous NaHCO3 solution (200 mL) with sonication
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-e40f6a014a414ff891b5d55fe3e18835
Source dataset
uspto-grants-2008_05
Patent number
US07368472B2

Reaction notes

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