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 1178589

반응식

HRID 1178589 반응식
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

참가 물질

6

반응물 3

HCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 99660384-[2-Amino-4-(4-methoxyphenyl)-1,3-thiazol-5-yl]-2-pyridylamine

생성물 1

HCID 9870905N-[4-(4-Methoxyphenyl)-5-{2-[(pyridine-3-carbonyl)amino]pyridin-4-yl}-1,3-thiazol-2-yl]pyridine-3-carboxamide수율 33%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 31374Dimethylacetamide용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e0e65aea05dd4ee1af7e29885f377c79
출처 데이터셋
uspto-grants-2007_10
특허 번호
US07276527B2

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