Trifluoroacetic acid → (+/-)-2-[1-(2-amino-2-methyl-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-one

HRID 1350622Notes

Reaction equation

HRID 1350622 reaction equation
C(OC(=O)[NH:7][C:8]([CH3:35])([CH3:34])[CH2:9][NH:10][CH:11]([C:15]1[N:24]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:23](=[O:32])[C:22]2[C:17](=[CH:18][C:19]([Cl:33])=[CH:20][CH:21]=2)[N:16]=1)[CH:12]([CH3:14])[CH3:13])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:7][C:8]([CH3:35])([CH3:34])[CH2:9][NH:10][CH:11]([C:15]1[N:24]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:23](=[O:32])[C:22]2[C:17](=[CH:18][C:19]([Cl:33])=[CH:20][CH:21]=2)[N:16]=1)[CH:12]([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69074256(2-[1-(3-Benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl)-carbamic acid tert-butyl ester

Product 1

HCID 21097057(+/-)-2-[1-(2-amino-2-methyl-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-oneYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (±)-{2-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-2-methyl-propylamino]-1,1-dimethyl-ethyl}-carbamic acid tert-butyl ester (1.62 g, 3.16 mmol) in dichloromethane (40 mL) was added trifluoroacetic acid (10 mL). The resultant solution was maintained at ambient temperature overnight and concentrated under reduced pressure. The residue was dissolved in dichloromethane (50 mL) and washed with saturated aqueous sodium bicarbonate (40 mL). The aqueous layer was extracted with dichloromethane (50 mL) and the combined extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure to give (±)-2-[1-(2-amino-2-methyl-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-3H-quinazolin-4-one (1.29 g, 99%) as a yellow solid which was used in the subsequent step without purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (40 mL)
  4. extractionThe aqueous layer was extracted with dichloromethane (50 mL)
  5. dry with materialthe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-78fd797b943148aab870baf3966e4f53
Source dataset
uspto-grants-2007_05
Patent number
US07214800B2

Reaction notes

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