Dichloromethane → HCID 66665919, compound

HRID 221769Notes

Reaction equation

HRID 221769 reaction equation
C(OC(=O)[NH:7][C:8]1[CH2:9][O:10][CH2:11][CH2:12][C:13]([C:19]2[CH:24]=[C:23]([NH:25][C:26]([C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][N:29]=3)=[O:27])[CH:22]=[CH:21][C:20]=2[F:36])([C:15]([F:18])([F:17])[F:16])[N:14]=1)(C)(C)C.[Cl:38]CCl>FC(F)(F)C(O)=O>[ClH:38].[NH2:7][C:8]1[CH2:9][O:10][CH2:11][CH2:12][C:13]([C:19]2[CH:24]=[C:23]([NH:25][C:26]([C:28]3[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][N:29]=3)=[O:27])[CH:22]=[CH:21][C:20]=2[F:36])([C:15]([F:18])([F:17])[F:16])[N:14]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 66665336HCID 66665336, compound

Product 1

HCID 66665919HCID 66665919, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

(5-{5-[(5-Cyano-pyridine-2-carbonyl)-amino]-2-fluoro-phenyl}-5-trifluoromethyl-2,5,6,7-tetrahydro-[1,4]oxazepin-3-yl)-carbamic acid tert-butyl ester (63.3, 0.121 mmol) was dissolved in 0.68 mL dichloromethane and 0.23 mL trifluoroacetic acid. The solution was stirred at for 45 minutes and then evaporated at room temperature. The residue was dissolved in EtOAc and extracted with saturated aqueous NaHCO3 solution. The layers were washed with brine and EtOAc. The combined organic layers were dried over Na2SO4 and evaporated. The crude product was dissolved in THF, 0.3 mL HCl solution 1 mol/L in diethyl ether was added and the mixture was evaporated. The residue was crystallized from wet ethanol and TBME to give 52.4 mg of the title compound as white crystals.

Workup

  1. customevaporated at room temperature
  2. dissolutionThe residue was dissolved in EtOAc
  3. extractionextracted with saturated aqueous NaHCO3 solution
  4. washThe layers were washed with brine and EtOAc
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. customevaporated
  7. dissolutionThe crude product was dissolved in THF
  8. addition0.3 mL HCl solution 1 mol/L in diethyl ether was added
  9. customthe mixture was evaporated
  10. customThe residue was crystallized from wet ethanol and TBME

Sources & evidence

ORD record
ord-f678c5ea71f54bf488b54f9ab78dfeac
Source dataset
uspto-grants-2012_06
Patent number
US08207164B2

Reaction notes

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