Morpholine → HCID 9870644, compound

HRID 1281711Notes

Reaction equation

HRID 1281711 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[CH2:38][CH2:37][O: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[CH2:38][CH2:37][O: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 8083MorpholineHCID 57191308HCID 57191308, compound

Product 1

HCID 9870644HCID 9870644, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Using an analogous procedure to that described in Example 3, a mixture of N-[3-(4diethylaminomethylbenzamido)-4-methylphenyl]-2-chloropyridine-4-carboxamide (0.5 g) and morpholine (5 ml) was stirred and heated to 110° 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), 2.2 (s, 3H), 2.44-2.49 (m, 4H), 3.42-3.57 (m. 4H), 3.6 (s, 2H), 3.65-3.63 (m, 4H), 7.08 (d, 1H), 7.2-7.25 (m, 2H), 7.45 (d, 2H), 7.58 (d, 1H), 7.79 (s, 1H), 7.92 (d, 2H), 8.26 (d, 1H), 9.83 (s, 1H), 10.28 (s, 1H); Mass Spectrum: M+H− 502.

Workup

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

Sources & evidence

ORD record
ord-e1780daf77a549cead221c7a6d9add84
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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