Hydrochloric Acid → HCID 69023929, compound

HRID 1007295Notes

Reaction equation

HRID 1007295 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]([CH:28]=[CH:29][C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[N:17]=1)=O)(C)(C)C.Cl>CO.C(OCC)(=O)C>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([CH:29]=[CH: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)=[CH:35][CH:34]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 69021907HCID 69021907, compound

Product 1

HCID 69023929HCID 69023929, compoundYield 90.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 520 mg of cis-N-tert-butoxycarbonyl-2-[2-(4-chlorostyryl)-6-methoxyquinazolin-4-yl]aminocyclohexylamine in 10 mL of methanol was combined with 5 mL of a 4 N solution of hydrogen chloride in ethyl acetate, and reacted at 50° C. for 24 hours. After the solvent was distilled off, the residue was basified by addition of a 10% aqueous solution of sodium hydroxide, and extracted with chloroform. After concentrating, the residue was purified by column chromatography on silica gel (chloroform:methanol=10:1) to obtain 378 mg of the desirable compound.

Workup

  1. customreacted at 50° C. for 24 hours
  2. distillationAfter the solvent was distilled off
  3. additionthe residue was basified by addition of a 10% aqueous solution of sodium hydroxide
  4. extractionextracted with chloroform
  5. concentrationAfter concentrating
  6. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-aa48c28094e14280a496f1dd76860b0e
Source dataset
uspto-grants-2004_09
Patent number
US06794389B2

Reaction notes

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