Pyrrolidine → N-(3-iodo-4-methylphenyl)-2-pyrrolidin-1-yl-isonicotinamide

HRID 2037246Notes

Reaction equation

HRID 2037246 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][N:14]=[C:13](Cl)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].[NH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[I:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:18])[C:11]2[CH:16]=[CH:15][N:14]=[C:13]([N:19]3[CH2:23][CH2:22][CH2:21][CH2:20]3)[CH:12]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 219145572-Chloro-N-(3-iodo-4-methylphenyl)pyridine-4-carboxamide2×

Product 1

HCID 21914627N-(3-iodo-4-methylphenyl)-2-pyrrolidin-1-yl-isonicotinamide

Procedure

A solution of N-(3-iodo-4-methylphenyl)-2-chloro-isonicotinamide (Intermediate 20) (7.00 g, 18.8 mmol) in pyrrolidine (20 ml) was heated at 80° C. under an atmosphere of nitrogen for 16 hours. Excess pyrrolidine was removed in vacuo and the residue was titurated with diethyl ether (20 ml). The resulting solid was collected by filtration and dried in vacuo to give N-(3-iodo-4-methylphenyl)-2-pyrrolidin-1-yl-isonicotinamide as a pale yellow solid (7.73 g, 18 mmol). LCMS: retention time 2.77 min MH+408. NMR: δH [2H6]-DMSO 10.29 (1H, s), 8.29 (1H, d), 8.20 (1H, d), 7.71 (1H, dd), 7.72 (1H, dd), 6.97 (1H, brd), 6.88 (1H, b), 3.45 (2H, apparent t), 3.09 (2H, m), 2.35 (3H, s), 1.98 (2H, m), 1.82 (2H, m).

Workup

  1. customExcess pyrrolidine was removed in vacuo
  2. filtrationThe resulting solid was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a9976e06fed24c83a907c766f87b9729
Source dataset
uspto-grants-2013_11
Patent number
US08575204B2

Reaction notes

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