4-Bromobenzoyl chloride → HCID 178439993, compound

HRID 855502Notes

Reaction equation

HRID 855502 reaction equation
[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([Br:18])=[N:16][NH:17][C:11]=2[N:10]=[C:9]1[CH:19]([NH:22][CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[CH2:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[Br:37][C:38]1[CH:46]=[CH:45][C:41]([C:42](Cl)=[O:43])=[CH:40][CH:39]=1>ClCCl>[CH2:1]([N:8]1[C:13](=[O:14])[C:12]2[C:15]([Br:18])=[N:16][NH:17][C:11]=2[N:10]=[C:9]1[CH:19]([N:22]([CH2:23][CH2:24][N:25]([CH3:27])[CH3:26])[C:42](=[O:43])[C:41]1[CH:45]=[CH:46][C:38]([Br:37])=[CH:39][CH:40]=1)[CH2:20][CH3:21])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 685154-Bromobenzoyl chlorideHCID 81531DiisopropylethylamineHCID 178457400HCID 178457400, compound

Product 1

HCID 178439993HCID 178439993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-benzyl-3-bromo-6-(1-{[2-(dimethylamino)ethyl]amino}propyl)-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one (1-4, 144 mg, 0.33 mmol, 1 equiv) and N,N-diisopropylethylamine (43 mg, 0.33 mol, 1 equiv) in dichloromethane (5 mL) was treated with 4-bromobenzoyl chloride (73 mg, 0.33 mmol, 1 equiv), and the resulting mixture was stirred under ambient conditions for 2 h. The reaction mixture was washed with saturated aqueous NaHCO3 solution, then brine, and dried (MgSO4) and concentrated. The residue was purified by flash chromatography. Elution with CH2Cl2 to 10% NH3-EtOH/CH2Cl2 gave N-[1-(5-benzyl-3-bromo-4-oxo-4,5-dihydro-1H-pyrazolo[3,4-d]pyrimidin-6-yl)propyl]-4-bromo-N-[2-(dimethylamino)ethyl]benzamide (1-5) as a colorless solid. 1H NMR (500 MHz, CDCl3) δ 10.9 (bs, 1H), 7.56 (m, 2H), 7.33 (m, 5H), 7.15 (m, 2H), 6.04 (d, J=15 Hz, 1H), 5.94 (m, 1H), 5.03 (d, J=15 Hz, 1H), 3.42 (m, 2H), 2.18 (m, 2H), 2.01 (m, 2H), 1.86 (s, 6H), 0.62 (m, 3H).

Workup

  1. washThe reaction mixture was washed with saturated aqueous NaHCO3 solution
  2. dry with materialbrine, and dried (MgSO4)
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography
  5. washElution with CH2Cl2 to 10% NH3-EtOH/CH2Cl2

Sources & evidence

ORD record
ord-38188dde4ac249a39d7072fa23143940
Source dataset
uspto-grants-2007_08
Patent number
US07262186B2

Reaction notes

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