Ethyl Bromide → HCID 24964732, compound

HRID 1161867Notes

Reaction equation

HRID 1161867 reaction equation
[CH:1]([NH:4][C:5](=[O:33])[CH2:6][N:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([N:18]3[CH2:24][CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:14]=2)[N:9]=[C:8]1[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1)([CH3:3])[CH3:2].[CH2:34](Br)[CH3:35].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:34]([N:21]1[CH2:22][CH2:23][CH2:24][N:18]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[N:9]=[C:8]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=2)[N:7]([CH2:6][C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:33])[C:16]3=[O:17])[CH2:19][CH2:20]1)[CH3:35]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 11430Potassium CarbonateHCID 59519020HCID 59519020, compound

Product 1

HCID 24964732HCID 24964732, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-isopropyl-2-[2-(3-methoxyphenyl)-4-oxo-6-perhydro-1,4-diazepin-1-yl-4H-quinazolin-3-yl]acetamide (EXAMPLE 2a) hydrochloride salt (50 mg, 0.103 mmol), ethyl bromide (22 mg, 0.21 mmol), and K2CO3 (43 mg, 0.31 mmol) in acetonitrile (5 mL) was heated to reflux for 24 h. The mixture was then cooled, filtered and concentrated in vacuo. The crude residue was purified by preparative HPLC to afford 2-[6-(4-ethylperhydro-1,4-diazepin-1-yl)-2-(3-methoxyphenyl)-4-oxo-4H-quinazolin-3-yl]-N-isopropylacetamide (EXAMPLE 4a) (5.1 mg, 0.010 mmol, 10%) as the hydrochloride salt.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 24 h
  3. temperatureThe mixture was then cooled
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-908b7fc54c1148d7aa284ce2398c0e40
Source dataset
uspto-grants-2010_10
Patent number
US07820649B2

Reaction notes

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