Acrylic Acid → N-[4-(3-Bromo-phenylamino)-7-(4-dimethylamino-butoxy)-quinazolin-6-yl]-acrylamide

HRID 507463

반응식

HRID 507463 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[N:8]=[CH:7][N:6]=[C:5]2[NH:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=1.[C:28](O)(=[O:31])[CH:29]=[CH2:30].CCN(CC)CC.Cl.CN(C)CCCN=C=NCC>CC(N(C)C)=O.C(Cl)Cl.CCOCC.CO.CCOC(C)=O.CCOC(C)=O.CCCCCC>[Br:27][C:23]1[CH:22]=[C:21]([NH:20][C:5]2[C:4]3[C:9](=[CH:10][C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])=[C:2]([NH:1][C:28](=[O:31])[CH:29]=[CH2:30])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:26]=[CH:25][CH:24]=1

참가 물질

9

반응물 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 106939126-amino-4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]quinazoline

생성물 1

HCID 10600888N-[4-(3-Bromo-phenylamino)-7-(4-dimethylamino-butoxy)-quinazolin-6-yl]-acrylamide수율 32%

시약·촉매·용매 4

HCID 31374Dimethylacetamide용매HCID 21226206Ethyl acetate hexane용매HCID 21584119Ethylacetate methanol용매HCID 21881112Ethyl ether methylene chloride용매

실험 절차

To a stirred solution of the above 6-aminoquinazoline (276 mg, 0.64 mmol), acrylic acid (6 mol eq., 3.85 mmol, 264 mL), and Et3N (excess, 1.0 mL) in DMA (10 mL) under N2 was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI.HCl) (3 mol eq., 1.92 mmol, 369 mg). The standard procedure above was followed to give after chromatography on grade III alumina eluting with EtOAc/hexane (1:1) to MeOH/EtOAc (3:97), N-[4-[(3-bromophenyl)amino]-7-[4-(N,N-dimethylamino)butyloxy]-quinazolin-6-yl]acrylamide (98 mg, 32%) as a cream powder, mp (CH2Cl2/Et2O) 112-115° C.

출처 및 근거

ORD 기록
ord-3e68c912f14d41b1822ac71bd63da872
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786131B2

연결된 노트

불러오는 중…