Triethylamine → HCID 58101114, compound

HRID 222630Notes

Reaction equation

HRID 222630 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]2[N:19]([CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[C:18]3[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=3[N:12]2[C:13](=[O:16])[C:14]=1[OH:15])=[O:8].C(N(CC)CC)C.[S:43](Cl)([CH3:46])(=[O:45])=[O:44]>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]2[N:19]([CH2:20][CH2:21][N:22]3[CH2:23][CH2:24][N:25]([S:43]([CH3:46])(=[O:45])=[O:44])[CH2:26][CH2:27]3)[C:18]3[CH:28]=[CH:29][CH:30]=[CH:31][C:17]=3[N:12]2[C:13](=[O:16])[C:14]=1[O:15][S:43]([CH3:46])(=[O:45])=[O:44])=[O:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 58100986HCID 58100986, compound

Product 1

HCID 58101114HCID 58101114, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Hydroxy-4-oxo-10-(2-piperazin-1-yl-ethyl)-4,10-dihydro-benzo[4,5]imidazo[1,2-a]pyrimidine-2-carboxylic acid, 3,4-dichloro-benzylamide (Example 15.5) (75 mg, 0.146 mmol) and triethylamine (60 μL, 0.31 mmol) were dissolved in dichloromethane (1 mL) and to this was added mesyl chloride (18 μL, 0.31 mmol). The reaction was stirred at room temperature for 15 minutes after which time the solvents were concentrated in vacuo and the residue purified by column chromatography (95:4.5:0.5 dichloromethane:methanol:aqueous ammonia) to afford the desired product (65 mg, 76%).

Workup

  1. concentrationwere concentrated in vacuo
  2. customthe residue purified by column chromatography (95:4.5:0.5 dichloromethane:methanol:aqueous ammonia)

Sources & evidence

ORD record
ord-def5985d2f454d3cab53ba850a77b538
Source dataset
uspto-grants-2012_06
Patent number
US08207334B2

Reaction notes

Loading…