Methacrylic Acid → HCID 18176145、化合物

HRID 507453ノート

反応式

HRID 507453 の反応式
[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

参加物

5

反応物 3

HCID 4093Methacrylic Acid2 回HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2 回HCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline

生成物 1

HCID 18176145HCID 18176145、化合物収率 24%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-68234d0f545f46a4858dd71363c7d102
出典データセット
uspto-grants-2010_08
特許番号
US07786131B2

反応ノート

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