Water → 4-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine

HRID 78310

反応式

HRID 78310 の反応式
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([O:11]C)=O)[CH:4]=1.[NH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.O>C1COCC1>[Cl:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9](=[O:11])[NH:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:4]=1

参加物

5

反応物 3

HCID 962WaterHCID 4082852-MorpholinoethylamineHCID 16655470Methyl 4-chloropyridine-2-carboxylate--hydrogen chloride (1/1)

生成物 1

HCID 236145794-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine収率 95.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 4-chloropyridine-2-carboxylate HCl salt (Method A2, Step 2; 1.01 g, 4.86 mmol) in THF (20 mL) was added 4-(2-aminoethyl)morpholine (2.55 mL, 19.4 mmol) dropwise and the resulting solution was heated at the reflux temp. for 20 h, cooled to room temp., and treated with water (50 mL). The resulting mixture was extracted with EtOAc (50 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure to afford 4-chloro-2-(N-(2-morpholin-4-ylethyl)carbamoyl)pyridine as a yellow oil (1.25 g, 95%): TLC (10% MeOH/90% EtOAc) Rf 0.50.

後処理

  1. temperaturethe resulting solution was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. extractionThe resulting mixture was extracted with EtOAc (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-ca6a6a4905ed4e3996dd133866f1f1e6
出典データセット
uspto-grants-2014_09
特許番号
US08841330B2

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