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

HRID 2044061ノート

反応式

HRID 2044061 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.).

後処理

  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)

出典と根拠

ORDレコード
ord-a3e815b8d3e747bda3923439036c1aac
出典データセット
uspto-grants-2013_11
特許番号
US08586751B2

反応ノート

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