Pyrrolidine → HCID 57325006, compound

HRID 1281710Notes

Reaction equation

HRID 1281710 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[CH:32]=[CH:31][C:10]([C:11]([NH:13][C:14]2[CH:15]=[C:16]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][N:27]=[C:26](Cl)[CH:25]=3)=[O:23])[CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2].[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1>O>[CH2:1]([N:3]([CH2:6][C:7]1[CH:32]=[CH:31][C:10]([C:11]([NH:13][C:14]2[CH:15]=[C:16]([NH:21][C:22]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([N:33]4[CH2:37][CH2:36][CH2:35][CH2:34]4)[CH:25]=3)=[O:23])[CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])=[CH:9][CH:8]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 57191308HCID 57191308, compound

Product 1

HCID 57325006HCID 57325006, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Using an analogous procedure to that described in Example 3, a mixture of N-[3-(4-diethylaminomethylbenzamido)-4-methylphenyl]-2-chloropyridine-4-carboxamide (0.5 g) and pyrrolidine (5 ml) was stirred and heated to 80° C. for 16 hours. The resultant solution was cooled to ambient temperature and poured into water. The resultant solid was isolated, washed with diethyl ether and dried under vacuum at 40° C. There was thus obtained the title compound (0.021 g); NMR Spectrum: (DMSOd6) 1.0 (t, 6H), 1.95 (m, 4H), 2.2 (s, 3H), 2.44-2.49 (m, 4H), 3.42-3.5 (m, 4H), 3.6 (s, 2H), 6.86 (s, 1H), 6.96 (d, 1H), 7.22 (d, 1H), 7.58 (d, 1H), 7.79 (s, 1H), 7.92 (d, 2H), 8.18 (d, 1H), 9.83 (s, 1H), 10.28 (s, 1H); Mass Spectrum: M+H+ 486.

Workup

  1. customThe resultant solid was isolated
  2. washwashed with diethyl ether
  3. customdried under vacuum at 40° C

Sources & evidence

ORD record
ord-025da4a5fab243468e675b82b8f3dda9
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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