3-Pyridinecarbonyl chloride, hydrochloride (1:1) → N-[4-(4-Methoxyphenyl)-5-{2-[(pyridine-3-carbonyl)amino]pyridin-4-yl}-1,3-thiazol-2-yl]pyridine-3-carboxamide

HRID 2212346

Reaction equation

Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.[NH2:11][C:12]1[S:13][C:14]([C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH2:31])[CH:26]=2)=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=2)[N:16]=1.[C:32](=[O:35])([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:24][O:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]2[N:16]=[C:12]([NH:11][C:32](=[O:35])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)[S:13][C:14]=2[C:25]2[CH:30]=[CH:29][N:28]=[C:27]([NH:31][C:2]([C:3]3[CH:4]=[N:5][CH:6]=[CH:7][CH:8]=3)=[O:9])[CH:26]=2)=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Nicotinoyl chloride hydrochloride (0.72 g, 4.1 mmol) and 4-dimethylaminopyridine (0.05 g, 0.4 mmol) were added to a solution of 4-[2-amino-4-(4-methoxyphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.41 g, 1.4 mmol) in N,N-dimethylacetamide (10 mL) and the mixture was stirred at 70° C. for 19 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added. The resulting crude crystals were collected by filtration and washed with water. The crude crystals were recrystallized from ethanol to obtain 0.23 g (0.44 mmol, yield 33%) of the title compound.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
filtrationThe resulting crude crystals were collected by filtration
washwashed with water
customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record: ord-97c70ef57e1046a68df529d66d38fed8
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101899B1

Linked notes

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