Potassium Carbonate → HCID 9872066, compound

HRID 1281714Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Cl[CH2:8][C:9]1[CH:10]=[C:11]([CH:37]=[CH:38][CH:39]=1)[C:12]([NH:14][C:15]1[CH:16]=[C:17]([NH:22][C:23]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)[CH:26]=2)=[O:24])[CH:18]=[CH:19][C:20]=1[CH3:21])=[O:13].[CH3:40][N:41]1[CH2:47][CH2:46][CH2:45][NH:44][CH2:43][CH2:42]1>O>[CH3:40][N:41]1[CH2:47][CH2:46][CH2:45][N:44]([CH2:8][C:9]2[CH:10]=[C:11]([CH:37]=[CH:38][CH:39]=2)[C:12]([NH:14][C:15]2[CH:16]=[C:17]([NH:22][C:23]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([N:31]4[CH2:36][CH2:35][O:34][CH2:33][CH2:32]4)[CH:26]=3)=[O:24])[CH:18]=[CH:19][C:20]=2[CH3:21])=[O:13])[CH2:43][CH2:42]1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (0.138 g) was added to a mixture of N-[3-(3-chloromethylbenzamido)-4-methylphenyl]-2-morpholinopyridine-4-carboxamide (0.232 g) and 1-methylhomopiperazine (1 ml) and the mixture was stirred and heated to 80° C. for 16 hours. The reaction mixture was allowed to cool to ambient temperature and water (25 ml) was added. The resultant solid was isolated, washed with water and dried under vacuum at 55° C. There was thus obtained the title compound (0.176 g); NMR Spectrum: (DMSOd6) 1.72 (m, 2H), 2.21 (s, 3H), 2.24 (s, 3H), 2.6 (m, 8H), 3.53 (m, 4H), 3.67 (s, 2H), 3.74 (m, 4H), 7.1 (d, 1H), 7.23 (m, 2H), 7.51 (m, 3H), 7.8 (s, 1H), 7.84 (d, 1H), 7.9 (s, 1H), 8.25 (d, 1H), 9.86 (s, 1H), 10.28 (s, 1H): Mass Spectrum: M+H 543.

Workup

temperatureto cool to ambient temperature
customThe resultant solid was isolated
washwashed with water
customdried under vacuum at 55° C

Sources & evidence

ORD record: ord-b102c9c6f08543ec83baccd269026401
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455520B1

Reaction notes

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