Ethyl chloroformate → 6-chloro-3,4-dihydro-2-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride

HRID 329725

反応式

HRID 329725 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([OH:16])=O)[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1.C(Cl)(=O)OCC.[NH2:23][CH:24]1[CH2:30][CH:29]2[N:31]([CH3:32])[CH:26]([CH2:27][CH2:28]2)[CH2:25]1.C(=O)([O-])O.[Na+]>O1CCCC1.CN(C)C=O.C(OCC)(=O)C.C(N(CC)CC)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH:23][CH:24]2[CH2:25][CH:26]3[N:31]([CH3:32])[CH:29]([CH2:28][CH2:27]3)[CH2:30]2)=[O:16])[C:5]2[O:10][CH:9]([CH3:11])[C:8](=[O:12])[NH:7][C:6]=2[CH:13]=1

参加物

9

反応物 4

HCID 10928Ethyl chloroformateHCID 4083948-Methyl-8-azabicyclo[3.2.1]octan-3-amineHCID 516892Sodium BicarbonateHCID 145172316-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid

生成物 1

HCID 198711806-chloro-3,4-dihydro-2-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride

試薬・触媒・溶媒 4

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4.8 g of 6-chloro-3,4-dihydro-2-methyl-3-oxo-2H-1,4-benzoxazine-8-carboxylic acid in 100 ml of tetrahydrofuran and 10 ml of dimethylformamide is cooled to below 0° C. and 5 ml of triethylamine is added under stirring thereto. Further, 2.5 g of ethyl chlorocarbonate is added and the mixture is stirred at room temperature for 45 minutes. To the resultant mixture is added 3.0 g of 3-amino-8-methyl-8-azabicyclo[3.2.1]octane and the mixture stirred for 4 hours. After completion of the reaction, aqueous sodium hydrogen carbonate and ethyl acetate are added. The organic layer is separated, washed with water and dried over magnesium sulfate. The solvent is distilled off and the residue is converted into the corresponding hydrochloride by treating with ethanolic hydrochloric acid followed by recrystallizing from ethanol-water to give 6-chloro-3,4-dihydro-2-methyl-N-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-3-oxo-2H-1,4-benzoxazine-8-carboxamide hydrochloride, melting at 325°-328° C. with decomposition.

後処理

  1. stirringthe mixture is stirred at room temperature for 45 minutes
  2. stirringthe mixture stirred for 4 hours
  3. additionare added
  4. customThe organic layer is separated
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. distillationThe solvent is distilled off
  8. additionby treating with ethanolic hydrochloric acid
  9. customby recrystallizing from ethanol-water

出典と根拠

ORDレコード
ord-32846653c30a4e1d8c2187d6ee8d761c
出典データセット
uspto-grants-1990_01
特許番号
US04892872

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