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4-Methylmorpholine → (3,5-difluoro(4-pyridyl))-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamide

HRID 1036092
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반응식

HRID 1036092 반응식
[F:1][C:2]1[CH:10]=[N:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.FC1C=CC=CC=1C([NH:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C:47]([CH3:55])=[CH:48][C:49]3[S:53][CH:52]=[N:51][C:50]=3[CH:54]=2)=[CH:42][N:41]=1)=O.C([O-])(O)=O.[Na+].CC(=O)OCC>C(Cl)Cl>[F:11][C:7]1[CH:8]=[N:9][CH:10]=[C:2]([F:1])[C:3]=1[C:4]([NH:39][C:40]1[CH:45]=[CH:44][C:43]([C:46]2[C:47]([CH3:55])=[CH:48][C:49]3[S:53][CH:52]=[N:51][C:50]=3[CH:54]=2)=[CH:42][N:41]=1)=[O:6]
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참가 물질

7

반응물 5

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 201118793,5-Difluoroisonicotinic acidHCID 58487026(2-fluorophenyl)-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamideHCID 86584982Sodium bicarbonate ethyl acetate

생성물 1

HCID 58487342
(3,5-difluoro(4-pyridyl))-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamide
수율 23.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A suspension of 3,5-difluoroisonicotinic acid (24 mg, 0.15 mmol), 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT)(35 mg, 0.2 mmol) and 45 μl N-methyl morpholine in 2 ml DCM was stirred at r.t. for 1 h before addition of 5-(6-methylbenzothiazol-5-yl)-2-pyridylamine (55) (24 mg, 0.1 mmol). The resulting reaction mixture was stirred at r.t. for overnight then at 50° C. for 3 h. The reaction mixture was worked up with aq. NaHCO3/EA. Org. phase was washed with brine, concentrated, subjected to silica flash column chromatography to furnish 8.9 mg (3,5-difluoro(4-pyridyl))-N-[5-(6-methylbenzothiazol-5-yl)(2-pyridyl)]carboxamide (58) as yellow semi-solid. (yield: 23.3%, purity>90%).

후처리

  1. customThe resulting reaction mixture
  2. waitat 50° C. for 3 h
  3. washphase was washed with brine
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6f4a51e647d34ba5a75ee2d6bb66455b
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08546403B2

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