1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-[4-(3-Bromo-phenylamino)-quinazolin-7-ylcarbamoyl]acrylic acid ethyl ester

HRID 507447노트

반응식

HRID 507447 반응식
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:20]([O:27][CH2:28][CH3:29])(=[O:26])/[CH:21]=[CH:22]/[C:23]([O-])=[O:24].Cl.CN(C)CCCN=C=NCC>CN(C)C=O>[CH2:28]([O:27][C:20](=[O:26])[CH:21]=[CH:22][C:23](=[O:24])[NH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1)[CH3:29]

참가 물질

5

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline2회HCID 58782252-Butenedioic acid, monoethyl ester

생성물 1

HCID 537015123-[4-(3-Bromo-phenylamino)-quinazolin-7-ylcarbamoyl]acrylic acid ethyl ester수율 23.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
5 °C

실험 절차

To an ice cold solution of 0.158 g of 7-amino-4-(3-bromoanilino)-quinazoline and 0.216 g of monoethyl fumarate in 3 mL of dry dimethylformamide was added 0.288 g of 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide HCl (EDAC). 7-Amino-4-(3-bromoanilino)-quinazoline can be made by methods well-known to those skilled in the art. See, for example, J Med Chem, 1995:3482, which is hereby incorporated by reference. After stirring at 5° C. for 5 minutes, the ice bath was removed, and the reaction was permitted to warm to room temperature where it stirred for 15 hours. The reaction was poured into cold water, and the suspension was made basic with the addition of a saturated sodium bicarbonate solution. The resulting solid was collected by filtration, washed with water, and then recrystallized from 50 mL of ethanol to afford 0.052 g of the desired product, mp >260° C.

후처리

  1. customthe ice bath was removed
  2. temperatureto warm to room temperature where it
  3. stirringstirred for 15 hours
  4. additionThe reaction was poured into cold water
  5. additionthe suspension was made basic with the addition of a saturated sodium bicarbonate solution
  6. filtrationThe resulting solid was collected by filtration
  7. washwashed with water
  8. customrecrystallized from 50 mL of ethanol

출처 및 근거

ORD 기록
ord-8507c21bdb4a4dc694ecbd0cf5fc59b5
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786131B2

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