Dichloromethane → 4-Amino-2-(4-methylbenzyl)-1-(4-quinazolin-4-yl-piperazin-1-yl)-butan-1-one dihydrochloride

HRID 1192441Notes

Reaction equation

HRID 1192441 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH:10]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][CH:31]=1)[C:11](=[O:28])[N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH2:14][CH2:13]1)(C)(C)C.C(Cl)[Cl:39]>Cl.O1CCOCC1>[ClH:39].[ClH:39].[NH2:7][CH2:8][CH2:9][CH:10]([CH2:29][C:30]1[CH:31]=[CH:32][C:33]([CH3:36])=[CH:34][CH:35]=1)[C:11]([N:12]1[CH2:13][CH2:14][N:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH2:16][CH2:17]1)=[O:28]

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67540421[3-(4-Methyl-benzyl)-4-oxo-4-(4-quinazolin-4-yl-piperazin-1-yl)-butyl]-carbamic acid tert-butyl ester

Product 1

HCID 675395884-Amino-2-(4-methylbenzyl)-1-(4-quinazolin-4-yl-piperazin-1-yl)-butan-1-one dihydrochloride

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture containing [3-(4-Methyl-benzyl)-4-oxo-4-(4-quinazolin-4-yl-piperazin-1-yl)-butyl]-carbamic acid tert-butyl ester (0.22 g, 0.44 mmol) in 10 mL of DCM and 5 mL of 4N HCl in dioxane was allowed to stir at room temperature under a nitrogen atmosphere overnight. The reaction was concentrated under reduced pressure. The residue was dissolved in methanol and ether added to precipitate the product. The solids were filtered and dried to afford 4-Amino-2-(4-methylbenzyl)-1-(4-quinazolin-4-yl-piperazin-1-yl)-butan-1-one dihydrochloride (167 mg.) LCMS (APCI+) m/z 404 [M+H]+; Rt: 1.87 min. 1H NMR (D2O, 400 MHz) δ 8.45 (1H, s), 7.87 (2H, t, J 8.1 Hz), 7.65-7.57 (2H, m), 7.01 (4H, s), 4.18-4.12 (1H, m), 3.98-3.92 (1H, m), 3.82-3.71 (2H, m), 3.52-3.37 (3H, m), 3.25-2.76 (6H, m), 2.64-2.54 (1H, m), 2.02 (3H, s), 1.98-1.80 (1H, m.)

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in methanol
  3. additionether added
  4. customto precipitate the product
  5. filtrationThe solids were filtered
  6. customdried

Sources & evidence

ORD record
ord-9445339959d7485289fddf57a7675a65
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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