4-Bromobenzoyl chloride → HCID 9915646, compound

HRID 855508Notes

Reaction equation

HRID 855508 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[CH2:11]([N:18]1[C:23](=[O:24])[C:22]2[N:25]=[CH:26][S:27][C:21]=2[N:20]=[C:19]1[CH:28]([NH:31][CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[CH2:29][CH3:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(N(CC)C(C)C)(C)C>ClCCl>[CH2:11]([N:18]1[C:23](=[O:24])[C:22]2[N:25]=[CH:26][S:27][C:21]=2[N:20]=[C:19]1[CH:28]([N:31]([CH2:32][CH2:33][N:34]([CH3:36])[CH3:35])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:29][CH3:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 58935445HCID 58935445, compound

Product 1

HCID 9915646HCID 9915646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromobenzoyl chloride (1 equiv) in dichloromethane is added to a solution of 6-benzyl-5-(1-{[2-(dimethylamino)ethyl]amino}-propyl)[1,3]thiazolo[5,4-d]pyrimidin-7(6H)-one (1-4, 1 equiv) and N,N-diisopropylethylamine (1 equiv) in dichloromethane, and the resulting mixture is stirred under ambient conditions for 1 h. The reaction mixture is washed with saturated aqueous NaHCO3 solution, and brine, then dried (MgSO4) and concentrated. The residue is purified by flash chromatography. Elution with CH2Cl2 to 5% NH3—EtOH/CH2Cl2 gives N-[1-(6-benzyl-7-oxo-6,7-dihydro[1,3]thiazolo[5,4-d]pyrimidin-5-yl)propyl]4-bromo-N-[2-(dimethylamino)ethyl]benzamide (1-5).

Workup

  1. washThe reaction mixture is washed with saturated aqueous NaHCO3 solution, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue is purified by flash chromatography
  5. washElution with CH2Cl2 to 5% NH3—EtOH/CH2Cl2

Sources & evidence

ORD record
ord-88a9b4328f0348118c958e55057274bc
Source dataset
uspto-grants-2007_08
Patent number
US07262187B2

Reaction notes

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