Triethylamine → HCID 23154095, compound

HRID 1175797Notes

Reaction equation

HRID 1175797 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:32]([NH:33][C:34](=[O:36])[CH3:35])=[C:13]3[C:14](=[O:31])[N:15]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]3=[N:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.[CH3:44][S:45](Cl)(=[O:47])=[O:46]>O1CCCC1>[CH3:44][S:45]([O:1][CH2:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:32]([NH:33][C:34](=[O:36])[CH3:35])=[C:13]3[C:14](=[O:31])[N:15]([CH2:22][C:23]4[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=4)[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[C:12]3=[N:11]2)=[CH:8][CH:9]=1)(=[O:47])=[O:46]

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 23154093HCID 23154093, compound

Product 1

HCID 23154095HCID 23154095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{2-[4-(2-hydroxyethyl)phenyl]-5-(4-methoxybenzyl)-4-oxo-4,5-dihydro-2H-pyrazolo[4,3-c]quinolin-3-yl}acetamide (3.2 g) and triethylamine (1.85 ml) in tetrahydrofuran (400 ml) was added dropwise methanesulfonyl chloride (0.77 ml) at 0° C. The mixture was stirred at room temperature for 5 hours, triethylamine (0.46 ml) and methanesulfonyl chloride (0.19 ml) were added thereto, and stirred again for 3 hours. The mixture was concentrated under reduced pressure, and to the residue was added ethyl acetate, washed with an aqueous sodium hydrogen carbonate solution, water, saturated brine, dried and concentrated under reduced pressure to obtain the target compound (3.5 g).

Workup

  1. stirringstirred again for 3 hours
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionto the residue was added ethyl acetate
  4. washwashed with an aqueous sodium hydrogen carbonate solution, water, saturated brine
  5. customdried
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2df63be8b01f4938930d6bdb24d1072a
Source dataset
uspto-grants-2010_11
Patent number
US07842701B2

Reaction notes

Loading…