Sodium Carbonate → HCID 59752513, compound

HRID 2106286Notes

Reaction equation

HRID 2106286 reaction equation
[CH2:1]([N:8]1[C:17]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12][C:11]=2[C:10]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[CH3:31][O:32][C:33](=[O:36])[CH2:34]Br>CC(C)=O>[CH3:31][O:32][C:33](=[O:36])[CH2:34][N:14]1[CH2:15][CH2:16][C:17]2[N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[N:9]=[C:10]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)[C:11]=2[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 60984Methyl bromoacetateHCID 11151899JNJ-18038683 free base

Product 1

HCID 59752513HCID 59752513, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1-benzyl-3-(4-chloro-phenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-azulene (Example 59, Step E; 1 mmol) in acetone (3 mL) was added Na2CO3 (2 mmol) and bromoacetic methyl ester (2 mmol). The mixture was stirred at RT for 1 h. After concentration and purification (SiO2, 2 M NH3 in MeOH/CH2Cl2), the title compound was obtained (60 mg). MS (ESI): exact mass calculated for C23H24ClN3O2, 409.16; found, m/z 410.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.44-7.42 (m, 2H), 7.31-7.29 (m, 2H), 7.25-7.23 (br m, 2H), 7.20-7.18 (br m, 1H), 7.02-6.99 (br m, 2H), 5.26 (s, 2H), 3.64 (s, 2H), 3.41 (s, 2H), 2.81-2.79 (br m, 4H), 2.75-2.73 (br m, 2H), 2.70-2.68 (br m, 2H).

Workup

  1. concentrationAfter concentration and purification (SiO2, 2 M NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-713cbfc50faa43dfa93719f9a2bd9f6c
Source dataset
uspto-grants-2009_08
Patent number
US07579470B2

Reaction notes

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