HCID 178483073, compound → HCID 178483070, compound

HRID 1984938Notes

Reaction equation

HRID 1984938 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([CH2:14][NH:15][C:16]2[N:25]=[C:24]([N:26]([CH3:28])[CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[NH2:7][C@@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][NH:15][C:16]2[N:25]=[C:24]([N:26]([CH3:28])[CH3:27])[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 1

HCID 178483073HCID 178483073, compound

Product 1

HCID 178483070HCID 178483070, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of cis-{4-[(4-dimethylamino-quinazolin-2-ylamino)-methyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.2 g, 3 mmol) in 50% TFA in CH2Cl2 (20 mL) was stirred at ambient temperature. After 30 minutes, the mixture was concentrated and the residue was diluted with 1 M aqueous sodium hydroxide. The aqueous layer was extracted with CH2Cl2 (twice). The combined organic layer was dried over Na2SO4, filtered and concentrated to give cis-N2-(4-amino-cyclohexylmethyl)-N4,N4-dimethyl-quinazoline-2,4-diamine (0.88 g, 98%) as a white solid.

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue was diluted with 1 M aqueous sodium hydroxide
  3. extractionThe aqueous layer was extracted with CH2Cl2 (twice)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae2c9e86f33e4a1488d15d62dd728e5f
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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