Triethylamine → HCID 60171602, compound

HRID 1520159Notes

Reaction equation

HRID 1520159 reaction equation
Cl.[CH3:2][NH:3][CH3:4].C(N(CC)CC)C.Cl[S:13]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]1[C:27]([C:40]3[CH:45]=[CH:44][C:43]([F:46])=[CH:42][CH:41]=3)=[N:28][C:29]3[C:34]([N:35]=1)=[CH:33][C:32]([C:36]([O:38][CH3:39])=[O:37])=[CH:31][CH:30]=3)[CH2:21][CH2:20][CH2:19]2)(=[O:15])=[O:14].C(OCC)(=O)C>ClCCl>[CH3:2][N:3]([CH3:4])[S:13]([C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[N:22]([C:26]1[C:27]([C:40]3[CH:41]=[CH:42][C:43]([F:46])=[CH:44][CH:45]=3)=[N:28][C:29]3[C:34]([N:35]=1)=[CH:33][C:32]([C:36]([O:38][CH3:39])=[O:37])=[CH:31][CH:30]=3)[CH2:21][CH2:20][CH2:19]2)(=[O:14])=[O:15]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 10473Dimethylamine, hydrochlorideHCID 86670035HCID 86670035, compound

Product 1

HCID 60171602HCID 60171602, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of dimethylamine hydrochloride (49.66 mg, 0.61 mmol) in dichloromethane (50 mL) was added and triethylamine (102 mg, 1.01 mmol) and stirred for 10 min. Then methyl 3-[6-(chlorosulfonyl)-1,2,3,4-tetrahydroquinolin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylate (260 mg, 0.51 mmol) in dichloromethane (20 mL) was added dropwise with stifling for 30 min at room temperature. The reaction mixture was concentrated under vacuum to give the residue, which was applied onto a silica gel column with 2%-5% ethyl acetate in petroleum ether to afford methyl 3-[6-(dimethylsulfamoyl)-1,2,3,4-tetrahydroquinolin-1-yl]-2-(4-fluorophenyl)quinoxaline-6-carboxylate as a yellow solid (240 mg, 91%).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customto give the residue, which

Sources & evidence

ORD record
ord-a7832eac7c3f44c3a5cdfa6b08b62da6
Source dataset
uspto-grants-2015_07
Patent number
US09073902B2

Reaction notes

Loading…