Triethylamine → HCID 18765927, compound

HRID 481009Notes

Reaction equation

HRID 481009 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]1[NH:11][C:12]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[C:13]([C:28]([O:30][CH3:31])=[O:29])[CH:14]([C:20]2[C:25]([Cl:26])=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:27])[C:15]=1[C:16]([O:18][CH3:19])=[O:17].[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(N(CC)CC)C>C(Cl)Cl>[Cl:27][C:21]1[CH:22]=[CH:23][CH:24]=[C:25]([Cl:26])[C:20]=1[CH:14]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[C:10]([CH2:9][CH2:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[NH:1][S:38]([CH3:37])(=[O:40])=[O:39])[NH:11][C:12]([CH2:32][C:33]([O:35][CH3:36])=[O:34])=[C:13]1[C:28]([O:30][CH3:31])=[O:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18765875HCID 18765875, compound

Product 1

HCID 18765927HCID 18765927, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of dimethyl 2-[2-(2-aminophenyl)ethyl]-4-(2,6-dichlorophenyl)-6-(2-methoxy-2-oxoethyl)-1,4-dihydro-3,5-pyridinedicarboxylate (500 mg/0.94 mmol) and methanesulfonyl chloride (107 mg/0.94 mmol) in anhydrous CH2Cl2(15 ml) was added triethylamine (94.7 mg/0.94 mmol) at 0° C. under nitrogen atmosphere. The resulting solution was stirred at room temperature for 1 day. The reaction was quenched with water and the separated organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated to afford a crude mixture. This crude was purified by column chromatography on silica gel (Hexane:EtOAc=3:2) to afford a yellow solid (262 mg/46%).

Workup

  1. customThe reaction was quenched with water
  2. washthe separated organic layer was washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4a6b8e3489b147f08c347610f3761e63
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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