Water → Ethyl 6-chloro-4-(thiophen-2-ylmethylamino)nicotinate

HRID 513277Notes

Reaction equation

HRID 513277 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([Cl:13])[CH:3]=1.[S:14]1[CH:18]=[CH:17][CH:16]=[C:15]1[CH2:19][NH2:20].CCN(C(C)C)C(C)C.O>CN1C(=O)CCC1.CCOC(C)=O>[Cl:13][C:4]1[CH:3]=[C:2]([NH:20][CH2:19][C:15]2[S:14][CH:18]=[CH:17][CH:16]=2)[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:6][N:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 34005(2-Thienylmethyl)amineHCID 81531DiisopropylethylamineHCID 600045Ethyl 4,6-dichloropyridine-3-carboxylate

Product 1

HCID 86664545Ethyl 6-chloro-4-(thiophen-2-ylmethylamino)nicotinateYield 100.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of ethyl 4,6-dichloronicotinate (1.14 g, 5.18 mmol), 2-thiophenemethylamine (0.530 mL, 5.17 mmol) and DIEA (1.80 mL, 10.3 mmol) in NMP (10 mL) was stirred at 90 C for 18 h. Water and EtOAc were added. The organic phase was washed with water, then was dried over Na2SO4, concentrated in vacuo to give ethyl 6-chloro-4-(thiophen-2-ylmethylamino)nicotinate as an oil (1.54 g).

Workup

  1. washThe organic phase was washed with water
  2. dry with materialwas dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9a13fd3e07b54ce28812175e5b07b24b
Source dataset
uspto-grants-2015_08
Patent number
US09102625B2

Reaction notes

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