Azasetron → HCID 131716241, 화합물

HRID 329749

반응식

HRID 329749 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH:17]2[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:18]2)=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1.ClC1C=CC=C(C(OO)=[O:33])C=1>C(Cl)(Cl)Cl>[OH2:10].[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH+:16]([O-:33])[CH:17]2[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:18]2)=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1.[Cl:1][C:2]1[CH:3]=[C:4]([C:14]([NH+:16]([CH:17]2[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:18]2)[O-:33])=[O:15])[C:5]2[O:10][CH2:9][C:8](=[O:11])[N:7]([CH3:12])[C:6]=2[CH:13]=1

참가 물질

4

반응물 2

HCID 2264AzasetronHCID 70297m-Chloroperbenzoic acid

생성물 1

HCID 131716241HCID 131716241, 화합물

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 5.0 g of 6-chloro-3,4-dihyro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide in 100 ml of chloroform with cooling at -30° C. is added 4.02 g of 80% metachloroperbenzoic acid, and the system stirred at -20° C. to -25° C. for about 30 minutes. The resultant solution is stirred at room temperature for 20 minutes and ammonia gas is bubbled into the solution at 10°-18° C. The precipitated crystals are filtered off and the filtrate is concentrated under reduced pressure. The residue is purified with column chromatography with a mixed eluent of chloroform and methanol (10:1) and to the residue is added acetonictile. The crystals are collected by filtration and recrystallized form acetonitrile to give 6-chloro-3,4-dihydro-4-methyl-3-oxo-N-(3-quinuclidinyl)-2H-1,4-benzoxazine-8-carboxamide N-oxide hemihydrate, melting at 198°-200° C. with decomposition.

후처리

  1. customammonia gas is bubbled into the solution at 10°-18° C
  2. filtrationThe precipitated crystals are filtered off
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. customThe residue is purified with column chromatography with a mixed eluent of chloroform and methanol (10:1) and to the residue
  5. additionis added acetonictile
  6. filtrationThe crystals are collected by filtration
  7. customrecrystallized
  8. customform acetonitrile

출처 및 근거

ORD 기록
ord-70babcd0159a493cbcafe0acc272effd
출처 데이터셋
uspto-grants-1990_01
특허 번호
US04892872

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