Methacrylic Acid → HCID 18176145, 화합물

HRID 507453노트

반응식

HRID 507453 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)(=[O:24])[C:21]([CH3:23])=[CH2:22].Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([NH:1][C:20](=[O:24])[C:21]([CH3:23])=[CH2:22])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

참가 물질

5

반응물 3

HCID 4093Methacrylic Acid2회HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2회HCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline

생성물 1

HCID 18176145HCID 18176145, 화합물수율 24%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 7-amino-4-[(3-bromo-phenyl)amino]quinazoline (J Med Chem, 1995;38:3482) (150 mg, 0.48 mmol) in dry DMF (20 mL) was added methacrylic acid (200 mg) and 1-(3-dimethylamino-propyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl) (2.5 mol, 228 mg), the reaction mixture was stirred overnight then further amounts of EDCI.HCl (230 mg) and methacrylic acid (200 mg) were added. After a further 2 days stirring the solvent was removed under vacuum and the residue diluted with saturated NaHCO3, extracted with ethyl acetate (EtOAc) and then the combined organic extracts were dried over anhydrous Na2SO4, concentrated under reduced pressure and chromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (5:45:50) to MeOH/CH2Cl2/EtOAc (10:40:50) to give N-[4-[(3-bromophenyl)amino]-quinazolin-7-yl]-2-methyl-acrylamide (43 mg, 24%) as a pale brown solid, mp (CH2Cl2/hexane) 255-259° C.

후처리

  1. stirringAfter a further 2 days stirring the solvent
  2. customwas removed under vacuum
  3. additionthe residue diluted with saturated NaHCO3
  4. extractionextracted with ethyl acetate (EtOAc)
  5. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customchromatographed on silica gel eluting with MeOH/CH2Cl2/EtOAc (5:45:50) to MeOH/CH2Cl2/EtOAc (10:40:50)

출처 및 근거

ORD 기록
ord-68234d0f545f46a4858dd71363c7d102
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786131B2

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