Trifluoroacetic acid → HCID 69022848, compound

HRID 1007301Notes

Reaction equation

HRID 1007301 reaction equation
C(OC([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]1[NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=2)[N:19]=[C:18]([NH:28][C:29](=[O:37])[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[N:17]=1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>C(Cl)Cl>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:29]([NH:28][C:18]2[N:17]=[C:16]([NH:15][C@H:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C@H:9]3[NH2:8])[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([O:26][CH3:27])[CH:24]=3)[N:19]=2)=[O:37])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69020964HCID 69020964, compound

Product 1

HCID 69022848HCID 69022848, compoundYield 82.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 120 mg of cis-N-tert-butoxycarbonyl-2-[2-(4-chlorobenzoylamino)-6-methoxyquinazolin-4-yl]aminocyclohexylamine in 5 mL of methylene chloride was combined with 2 mL of trifluoroacetic acid, and reacted at room temperature for 1 hour. The reaction solution was basified by addition of a saturated solution of sodium hydrogen carbonate, extracted with chloroform, and dried. After the solvent was distilled off, the residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to obtain 80 mg of the desirable compound.

Workup

  1. customreacted at room temperature for 1 hour
  2. extractionextracted with chloroform
  3. customdried
  4. distillationAfter the solvent was distilled off
  5. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-1a5665148ce34deca1bc1aa7e87ceb64
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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