Benzyl Bromide → HCID 57794685, compound

HRID 2099779Notes

Reaction equation

HRID 2099779 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([NH:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][C:28]2=[O:37])[CH2:23][CH2:22]1)=[O:20])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([CH3:17])[CH:16]=1)[NH:13][N:12]=[CH:11]2.[CH2:38](Br)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>CS(C)=O>[CH2:38]([N:3]1[CH:4]=[CH:5][N:1]=[C:2]1[CH:6]([NH:18][C:19]([N:21]1[CH2:26][CH2:25][CH:24]([N:27]2[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[NH:29][C:28]2=[O:37])[CH2:23][CH2:22]1)=[O:20])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[C:15]([CH3:17])[CH:16]=1)[NH:13][N:12]=[CH:11]2)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 11409395HCID 11409395, compound

Product 1

HCID 57794685HCID 57794685, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(1-(1H-Imidazol-2-yl)-2-(7-methyl-1H-indazol-5-yl)ethyl)-4-(2-oxo-1,2-dihydroquinazolin-3(4H)-yl)piperidine-1-carboxamide (100 mg, 0.2 mmol) and benzyl bromide (25.0 μL, 1.1 equiv) were combined in dimethyl sulfoxide (0.6 mL). After stirring at room temperature for 16 h, the reaction mixture was poured into ice water and extracted with ethyl acetate (2×). The organic layer was washed with brine (2×), dried over sodium sulfate, concentrated, and purified by column chromatography to afford 14.0 mg (12%). 1H-NMR (CD3OD, 500 MHz) δ 1.58-1.70 (m, 4H), 2.48 (s, 3H), 2.75-2.84 (m, 2H), 3.36-3.43 (m, 2H), 4.02-4.14 (m, 3H), 4.23 (s, 2H), 4.86 (m, 1H), 5.23 (s, 2H), 5.29-5.38 (m, 1H), 6.85-7.01 (m, 3H), 7.10-7.84 (m, 10H), 7.96 (s, 1H). Mass spec.: 589.16 (MH)+.

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. washThe organic layer was washed with brine (2×)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by column chromatography
  6. customto afford 14.0 mg (12%)

Sources & evidence

ORD record
ord-dbb83d8fe1734b3db0e6e9c4968538a1
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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