Hydrochloric Acid → HCID 68846891, compound

HRID 1984914Notes

Reaction equation

HRID 1984914 reaction equation
C(OC(=O)[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([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)[CH2:11][CH2:10]1)(C)(C)C.Cl.[OH-].[Na+]>CCOC(C)=O>[NH2:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([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)[CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 178483080HCID 178483080, compound

Product 1

HCID 68846891HCID 68846891, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a suspension of trans-[4-(4-dimethylamino-quinazolin-2-ylamino)-cyclohexylmethyl]-carbamic acid tert-butyl ester obtained in step B of example 6 (400 mg, 1.00 mmol) in EtOAc (10 mL) was added 4 M hydrogen chloride in EtOAc (5 mL). The mixture was stirred at ambient temperature for 80 min. The reaction mixture was alkalized with 2 M aqueous sodium hydroxide, and the aqueous layer was extracted with CHCl3 (three times). The combined organic layer was dried over MgSO4, filtered, concentrated, purified by medium-pressure liquid chromatography (NH-silica gel, 33% EtOAc in hexane to 3% MeOH in CHCl3) to give N2-(4-aminomethyl-cyclohexyl)-N4,N4-dimethyl-quinazoline-2,4-diamine (250 mg, 83%) as a pale yellow oil.

Workup

  1. extractionthe aqueous layer was extracted with CHCl3 (three times)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by medium-pressure liquid chromatography (NH-silica gel, 33% EtOAc in hexane to 3% MeOH in CHCl3)

Sources & evidence

ORD record
ord-042869392d684a03bc35fb9a48d96169
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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