Nicotinic Acid → HCID 53766110, compound

HRID 2117471Notes

Reaction equation

HRID 2117471 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][NH:13][CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)=[CH:8][CH:9]=1)=[O:4].C1CCC(N=C=NC2CCCCC2)CC1.[C:39](O)(=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[N:42][CH:41]=1>C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([CH2:10][CH2:11][CH2:12][N:13]([CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[C:39]([C:40]2[CH:41]=[N:42][CH:43]=[CH:44][CH:45]=2)=[O:46])=[CH:8][CH:9]=1)=[O:4]

Participants

5

Reactant 3

HCID 938Nicotinic AcidHCID 10868DicyclohexylcarbodiimideHCID 539001205-(3-(3-(3-Chloro-phenyl)-propylamino)-propyl)-thiophene-2-carboxylic acid methyl ester

Product 1

HCID 53766110HCID 53766110, compoundYield 116.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-(3-(3-(3-chloro-phenyl)-propylamino)-propyl)-thiophene-2-carboxylic acid methyl ester (from Preparation 8, 0.075 g, 0.213 mmol), DCC (0.0483 g 0.234 mmol) and nicotinic acid (0.0289 g, 0.234 mmol) in 10 mL CH2Cl2 was stirred at room temperature overnight. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was dissolved in 15 mL EtOAc and the insolubles were removed via filtration. The organic solution was washed with water followed by brine, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound of Step A as an oil (113 mg). MS 457 (M+).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. dissolutionThe residue was dissolved in 15 mL EtOAc
  4. customthe insolubles were removed via filtration
  5. washThe organic solution was washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e71b41cd777b44f0827c3d05eb310368
Source dataset
uspto-grants-2008_10
Patent number
US07442702B2

Reaction notes

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