Triethylamine → 2-{[2-(2,5-dioxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-N-(3-trifluoromethyl-phenyl)-benzamide

HRID 2110173Notes

Reaction equation

HRID 2110173 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)=[O:13])[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[C:36](Cl)(=[O:42])[CH2:37][CH2:38][C:39](Cl)=[O:40]>ClCCl>[O:40]=[C:39]1[CH2:38][CH2:37][C:36](=[O:42])[N:1]1[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:28]=[CH:27][CH:26]=[CH:25][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[CH:16]=2)=[O:13])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10970Succinyl chlorideHCID 121352662-[(2-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide

Product 1

HCID 121447002-{[2-(2,5-dioxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-N-(3-trifluoromethyl-phenyl)-benzamideYield 51.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

193 mg (0.5 mmol) of 2-[(2-amino-pyridin-4-ylmethyl)-amino]-N-(3-trifluoromethyl-phenyl)-benzamide is mixed in 20 ml of dichloromethane with 0.21 ml (1.5 mmol) of triethylamine, and it is mixed at room temperature drop by drop with a solution of 93 mg (0.6 mmol) of succinic acid dichloride in 3 ml of methylene chloride. After stirring overnight at room temperature, it is diluted with methylene chloride and washed in succession with water, saturated sodium bicarbonate solution and saturated common salt solution. Then, the organic phase is dried, filtered and concentrated by evaporation. The residue is chromatographed on Isolute (Separtis Company) with a gradient of methylene chloride:ethanol=100:0 to 95:5. 120 mg (51% of theory) of 2-{[2-(2,5-dioxo-pyrrolidin-1-yl)-pyridin-4-ylmethyl]-amino}-N-(3-trifluoromethyl-phenyl)-benzamide is obtained. (MS: m/e 468)

Workup

  1. washwashed in succession with water, saturated sodium bicarbonate solution and saturated common salt solution
  2. customThen, the organic phase is dried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on Isolute (Separtis Company) with a gradient of methylene chloride

Sources & evidence

ORD record
ord-6371552f792841c78dda67343379b5ab
Source dataset
uspto-grants-2009_04
Patent number
US07517894B2

Reaction notes

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