N-BOC-ethylenediamine → HCID 10048021, compound

HRID 1271884Notes

Reaction equation

HRID 1271884 reaction equation
C(O[C:6](=O)[NH:7][CH2:8][CH2:9][NH:10][CH:11]([C:14]1[N:23]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22](=[O:31])[C:21]2[C:16](=[CH:17][C:18]([Cl:32])=[CH:19][CH:20]=2)[N:15]=1)[CH2:12][CH3:13])(C)(C)C.C(N1[C:50](=[O:51])[C:49]2C(=CC(Cl)=CC=2)N=C1C(Br)CC)C1C=CC=CC=1.C(OC(=O)NCCN)(C)(C)C.C(=O)(O)[O-].[Na+]>CCO>[CH2:24]([N:23]1[C:22](=[O:31])[C:21]2[C:16](=[CH:17][C:18]([Cl:32])=[CH:19][CH:20]=2)[N:15]=[C:14]1[CH:11]([N:10]1[C:50](=[O:51])[CH2:49][CH2:6][NH:7][CH2:8][CH2:9]1)[CH2:12][CH3:13])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 4

HCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 184550303-Benzyl-2-(1-bromopropyl)-7-chloroquinazolin-4(3H)-oneHCID 69478431HCID 69478431, compound

Product 1

HCID 10048021HCID 10048021, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Preparation of {2-[1-(3-benzyl-7-chloro-4-oxo-3,4-dihydro-quinazolin-2-yl)-propylamino]-ethyl}-carbamic acid tert-butyl ester: A mixture of 3-benzyl-2-(1-bromo-propyl)-7-chloro-3H-quinazolin-4-one (3.9 g, 10 mmol) (WO 0130768), (2-amino-ethyl)-carbamic acid tert-butyl ester (2.40 g, 15 mmol) and sodium bicarbonate (1.26 g, 15 mmol) in EtOH (50 mL) was refluxed overnight. The salts were removed by filtration and the filtrate was concentrated to dryness. The residue which remained was purified by flash chromatography on silica gel (10–15% EtOH in hexane) to give the title compound (2.90 g) as a white solid: MS (ES) m/e 471.2 (M+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. customThe salts were removed by filtration
  3. concentrationthe filtrate was concentrated to dryness
  4. customThe residue which remained was purified by flash chromatography on silica gel (10–15% EtOH in hexane)

Sources & evidence

ORD record
ord-1b21b5a7e580453d8e1ea1f13963e52f
Source dataset
uspto-grants-2007_04
Patent number
US07208487B2

Reaction notes

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