4-Bromobenzoyl chloride → HCID 10153573, compound

HRID 2224102Notes

Reaction equation

HRID 2224102 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[C:25]([Br:29])=[C:26]([Br:28])[S:27][C:21]=2[N:20]=[C:19]1[CH:30]([NH:33][CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[CH2:31][CH3:32])[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[C:25]([Br:29])=[C:26]([Br:28])[S:27][C:21]=2[N:20]=[C:19]1[CH:30]([N:33]([CH2:34][CH2:35][N:36]([CH3:38])[CH3:37])[C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([Br:1])=[CH:3][CH:4]=1)[CH2:31][CH3:32])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 59716440HCID 59716440, compound

Product 1

HCID 10153573HCID 10153573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-bromobenzoyl chloride (19 mg, 0.085 mmol, 1 equiv) in dichloromethane (1 mL) was added to a solution of 3-benzyl-5,6-dibromo-2-(1-{[2-(dimethylamino)ethyl]amino}propyl)thieno[2,3-d]pyrimidin-4(3H)-one (2-7, 45 mg, 0.085 mmol, 1 equiv) and N,N-diisopropylethylamine (11 mg, 0.085 mmol, 1 equiv) in dichloromethane (5 mL), and the resulting reaction mixture was stirred under ambient conditions for 1 h. The reaction mixture was washed with saturated aqueous NaHCO3 solution, then brine, and dried (MgSO4) and concentrated. The residue was purified by reverse-phase LC (H2O/CH3CN gradient w/0.1% TFA present) to provide N-[1-(3-benzyl-5,6-dibromo-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidin-2-yl)propyl]-4-bromo-N-[2-(dimethylamino)ethyl]benzamide (2-9) as a colorless foam. MS(M+1)=708.9

Workup

  1. customthe resulting reaction mixture
  2. washThe reaction mixture was washed with saturated aqueous NaHCO3 solution
  3. dry with materialbrine, and dried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by reverse-phase LC (H2O/CH3CN gradient w/0.1% TFA present)

Sources & evidence

ORD record
ord-868fc35700544a5293886c639af9519e
Source dataset
uspto-grants-2008_05
Patent number
US07378411B2

Reaction notes

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