Ammonium Hydroxide → 6-Chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide

HRID 2044036ノート

反応式

HRID 2044036 の反応式
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[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.[NH4+].[OH-].C([N:30](C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.[Li+].[Cl-]>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:30])=[O:8])=[C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([C:18]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:19])=[CH:16][CH:17]=2)[N:3]=1

参加物

7

反応物 4

HCID 14923Ammonium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2 回HCID 574896006-Chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinic acid

生成物 1

HCID 574896016-Chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide収率 94.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 433294Lithium Chloride溶媒

実験手順

To a solution of 6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinic acid (6.60 g, 18.24 mmol), NH4OH (40.1 mL, 20.07 mmol), and N-ethyl-N-isopropylpropan-2-amine (3.54 g, 27.4 mmol) in DMF (40 mL) was added HATU (13.87 g, 36.5 mmol) at rt. The solution became cloudy but eventually cleared up as the HATU was added. The reaction was completed after 1 h. The reaction mixture was diluted with 10% LiCl and extracted with ethyl acetate three times. The organic extracts was washed with 10% LiCl, water twice, and then concentrated. The light yellow solid was triturated with CH2Cl2 to give 3.8 g. A second trituration gave 1.95 g, and a third trituration gave 462 mg. A total of 6.2 g of 6-chloro-2-(4-(morpholine-4-carbonyl)phenylamino)nicotinamide was obtained.

後処理

  1. additionwas added
  2. extractionextracted with ethyl acetate three times
  3. washThe organic extracts was washed with 10% LiCl, water twice
  4. concentrationconcentrated
  5. customThe light yellow solid was triturated with CH2Cl2
  6. customto give 3.8 g
  7. customA second trituration gave 1.95 g
  8. customa third trituration gave 462 mg

出典と根拠

ORDレコード
ord-2e71f5b679ed4947b75ee1a4095eb101
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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