N-bromobutanimide → 5-Bromo-6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide

HRID 2044061노트

반응식

HRID 2044061 반응식
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:14][CH:13]=2)[N:3]=1.C1C(=O)N([Br:33])C(=O)C1.OS([O-])=O.[Na+]>C(#N)C.C(OCC)(=O)C>[Br:33][C:10]1[C:2]([Cl:1])=[N:3][C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[O:19])=[CH:16][CH:17]=2)=[C:5]([CH:9]=1)[C:6]([NH2:8])=[O:7]

참가 물질

6

반응물 3

HCID 67184N-bromobutanimideHCID 23665763Sodium BisulfiteHCID 574896016-Chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide

생성물 1

HCID 574896165-Bromo-6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide수율 38.6%

시약·촉매·용매 2

HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A suspension of 6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide (500 mg, 1.385 mmol) and NBS (250 mg, 1.4 mmol) in acetonitrile (10 mL) was stirred at overnight. The reaction mixture was treated with 1M NaHSO3 and stirred at rt for 2 h. Next, the reaction mixture was diluted with ethyl acetate and the precipitate filtered to give a solid. The organic layer of the filtrate was separated and concentrated to an additional amount of solid. The above solids were combined and triturated with 250 mL of MeOH/CH2Cl2 (˜1:1 ratio) to give 235 mg of 5-bromo-6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide as a grey solid. LCMS: (M+H)+=338.80, 440.83, 442.87 (Br, Cl pattern). 1H NMR (400 MHz, methanol-d3-MIX) δ ppm 8.38 (1H, s), 7.77 (2H, d, J=8.35 Hz), 7.42 (2H, d, J=8.79 Hz), 3.69 (8H, br. s.).

후처리

  1. stirringstirred at rt for 2 h
  2. filtrationthe precipitate filtered
  3. customto give a solid
  4. customThe organic layer of the filtrate was separated
  5. concentrationconcentrated to an additional amount of solid
  6. customtriturated with 250 mL of MeOH/CH2Cl2 (˜1:1 ratio)

출처 및 근거

ORD 기록
ord-a3e815b8d3e747bda3923439036c1aac
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586751B2

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