Pyridine → HCID 68467898, compound

HRID 453488Notes

Reaction equation

HRID 453488 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:26])[C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([Cl:25])[CH:19]=2)=[CH:12][CH:11]=1.N1C=CC=CC=1.[C:41](Cl)(=[O:48])[C:42]1[CH:47]=[CH:46][CH:45]=[N:44][CH:43]=1>C(Cl)Cl.O>[Cl:25][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][C:21]=1[Cl:24])[C:17]([NH:16][C:13]1[CH:12]=[CH:11][C:10]([O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:4][C:3]=2[CH2:2][NH:1][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][CH:45]=[N:44][CH:43]=2)=[CH:15][CH:14]=1)=[O:26]

Participants

6

Reactant 3

HCID 1049PyridineHCID 82604Nicotinoyl chlorideHCID 68470120Tert-butyl 2-(3-(aminomethyl)-4-(4-(3,4-dichlorobenzamido)phenoxy)phenyl)acetate

Product 1

HCID 68467898HCID 68467898, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

The product of step C (0.050 g, 0.997 mmol) was dissolved into 1 mL of DCM in a small test tube. Pyridine (0.017 g, 0.219 mmol) and nicotinoyl chloride (0.0195 g, 0.110 mmol) were added, and the reaction mixture was stirred for 12 hours. The reaction mixture was then diluted with methylene chloride and water. The methylene chloride layer was separated and loaded directly onto a biotage 12i column eluting with methylene chloride:MeOH (95:5) to yield tert-butyl 2-(4-(4-(3,4-dichlorobenzamido)phenoxy)-3-(nicotinamidomethyl)phenyl)-acetate (44 mg, 73% yield) as a clear oil.

Workup

  1. customThe methylene chloride layer was separated
  2. washeluting with methylene chloride:MeOH (95:5)

Sources & evidence

ORD record
ord-42c502a64c1243ce9ce26785824da346
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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