Diisopropylethylamine → N-[4-(Benzyloxy)phenyl]-7-fluoro-6-[5-({[2-(methanesulphonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine

HRID 51152

반응식

HRID 51152 반응식
Cl.[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([F:34])=[C:24]([C:27]4[O:31][C:30]([CH:32]=O)=[CH:29][CH:28]=4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.[CH3:44][S:45]([CH2:48][CH2:49][NH2:50])(=[O:47])=[O:46].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(O)(=O)C>[CH2:2]([O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([F:34])=[C:24]([C:27]4[O:31][C:30]([CH2:32][NH:50][CH2:49][CH2:48][S:45]([CH3:44])(=[O:47])=[O:46])=[CH:29][CH:28]=4)[CH:25]=3)[N:20]=[CH:19][N:18]=2)=[CH:12][CH:11]=1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 43405612-(Methylsulfonyl)ethanamineHCID 5049666Sodium triacetoxyborohydrideHCID 219520395-(4-(4-Benzyloxy-phenylamino)-7-fluoro-quinazolin-6-yl)-furan-2-carbaldehyde hydrochloride

생성물 1

HCID 9872163N-[4-(Benzyloxy)phenyl]-7-fluoro-6-[5-({[2-(methanesulphonyl)ethyl]amino}methyl)-2-furyl]-4-quinazolinamine수율 61%

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 176Acetic Acid용매

실험 절차

Prepared according to Procedure D from a mixture of 5-(4-(4-benzyloxy-phenylamino)-7-fluoro-quinazolin-6-yl)-furan-2-carbaldehyde hydrochloride (0.13 grams) in 1,2-dichloroethane (3 ml), diisopropylethylamine (65 mg), acetic acid (45 mg), 2-methanesulphonylethylamine (0.125 grams), and sodium triacetoxyborohydride (0.27 grams). The mixture was stirred for 18 hours. The reaction mixture was quenched with methanol (3 ml) and poured into a separatory funnel containing aqueous saturated sodium hydrogen carbonate (100 ml) and ethyl acetate (100 ml). The mixture was extracted. The organic layer was washed with water. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was treated with ethyl acetate/hexanes and collected by filtration (0.083 g, 61% yield). δ1H NMR (400 MHz, DMSO-d6) 9.98(s, 1H), 8.83(d, 1H), 8.44(s, 1H), 7.58(m, 3H), 7.44(m, 2H), 7.37(m, 2H), 7.31(m, 1H), 7.03(d, 1H), 6.91(m, 1H), 6.5(d, 1H), 5.1(s, 2H), 3.84(s, 1H), 3.25(m, 2H), 2.99(s, 3H), 2.96(m, 2H). ESI-MS m/z 545(M−1).

후처리

  1. customPrepared
  2. customThe reaction mixture was quenched with methanol (3 ml)
  3. additionpoured into a separatory funnel
  4. additioncontaining aqueous saturated sodium hydrogen carbonate (100 ml) and ethyl acetate (100 ml)
  5. extractionThe mixture was extracted
  6. washThe organic layer was washed with water
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. additionThe residue was treated with ethyl acetate/hexanes
  11. filtrationcollected by filtration (0.083 g, 61% yield)

출처 및 근거

ORD 기록
ord-3d4a223874ec4d73a82e2cc9e7372ab2
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713485B2

연결된 노트

불러오는 중…