Triethylamine → 2-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724966노트

반응식

HRID 724966 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19]O)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.S(Cl)([Cl:25])=O.C(N(CC)CC)C.[OH-].[Na+]>C(Cl)(Cl)Cl.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH2:19][Cl:25])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 10615550HCID 10615550, 화합물

생성물 1

HCID 108307382-chloro-8-chloromethyl-5,11-dihydro-11-ethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one수율 94.5%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 57417360Sodium chloride; water용매

실험 절차

The 2-chloro-5,11-dihydro-11-ethyl-8-hydroxymethyl-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.52 g, 1.6 mmol) was dissolved in chloroform (10 mL) and treated with thionyl chloride (0.12 mL, 1.6 mmol) followed by triethylamine (0.23 mL, 1.6 mmol). After 0.5 hours stirring the mixture was made alkaline with 15% aqueous sodium hydroxide, diluted with brine (10 mL) and the organic layer was separated. The aqueous layer was then extracted with dichloromethane (2×20 mL). The combined organics were dried over sodium sulfate, filtered, concentrated and the residue was purified by flash chromatography (gradient hexanes to 1:1 hexanes/ethyl acetate) to give the title compound (0.51 g, 93%), m.p. 133°-134° C.

후처리

  1. customthe organic layer was separated
  2. extractionThe aqueous layer was then extracted with dichloromethane (2×20 mL)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography (gradient hexanes to 1:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-74783ae67d934ed89557648205037a90
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705499

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