3-Methyl-4-phenoxyaniline → 2-Chloro-N-{3-[4-(3-methyl4-phenoxy-phenylamino)-quinazolin-6-yl]-prop-2-ynyl}-acetamide

HRID 1264064ノート

反応式

HRID 1264064 の反応式
[Cl:1][CH2:2][C:3]([NH:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]=[C:12]2Cl)=[O:4].[CH3:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][C:27]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[NH2:24]>ClCCCl.C(O)(C)(C)C.C(OCC)(=O)C>[Cl:1][CH2:2][C:3]([NH:5][CH2:6][C:7]#[C:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[N:15]=[CH:14][N:13]=[C:12]2[NH:24][C:23]1[CH:25]=[CH:26][C:27]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[C:21]([CH3:20])[CH:22]=1)=[O:4]

参加物

6

反応物 2

HCID 155504883-Methyl-4-phenoxyanilineHCID 224843152-Chloro-N-(3-(4-chloroquinazolin-6-yl)prop-2-yn-1-yl)acetamide

生成物 1

HCID 541744332-Chloro-N-{3-[4-(3-methyl4-phenoxy-phenylamino)-quinazolin-6-yl]-prop-2-ynyl}-acetamide収率 94%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6386tert-Butanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 2-Chloro-N-[3-(4-chloro-quinazolin-6-yl)-prop-2-ynyl]-acetamide (50 mg; 0.17mmol) and 3-methyl-4-phenoxyaniline (36 mg; 0.9 equiv.) in 1,2-dichloroethane (1 ml) and t-butanol (1 ml) was heated at 87° C. for 30 minutes. The mixture was then cooled to room temperature and diluted with ethyl acetate to further facilitate precipitation. The solution was then filtered to give the coupled product as a yellow powder (73 mg; 90%). 2.28 (3H, s), 4.10 (2H, s), 4.30 (2H, s), 6.93 (3H, d), 7.09 (1H, t), 7.34 (2H, t), 7.50-7.53 (1H, dd, J=2.6, 6 Hz), 7.63 (1H, d, J=2.4 Hz), 7.78 (I H, d, J=8 Hz), 8.06-8.08 (1H, dd, J=1.4, 7.2 Hz), 8.68 (1H, d, J=1.2 Hz), 8.75 (1H, s). Irms(M+): 457.0, 4.59.1; (M−): 455.7, 419.6

後処理

  1. filtrationThe solution was then filtered

出典と根拠

ORDレコード
ord-51764cd995ea4b27949780744fc95d38
出典データセット
uspto-grants-2003_04
特許番号
US06541481B2

反応ノート

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