3-Methyl-4-(pyridin-3-yloxy)aniline → 2-Chloro-N-(3-{4-[3-methyl-4-(pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-acetamide

HRID 2180975ノート

反応式

HRID 2180975 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]([NH2:34])[CH:24]=[CH:25][C:26]=1[O:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1>CC(O)(C)C.ClCCCl>[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:34][C:23]1[CH:24]=[CH:25][C:26]([O:27][C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[C:21]([CH3:20])[CH:22]=1)=[O:4]

参加物

4

反応物 2

HCID 219252673-Methyl-4-(pyridin-3-yloxy)anilineHCID 224843152-Chloro-N-(3-(4-chloroquinazolin-6-yl)prop-2-yn-1-yl)acetamide

生成物 1

HCID 224841242-Chloro-N-(3-{4-[3-methyl-4-(pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-acetamide収率 88.8%

試薬・触媒・溶媒 1

HCID 21868497Tert-butyl alcohol 1,2-dichloroethane溶媒

実験手順

A mixture of 2-Chloro-N-[3-(4-chloro-quinazolin-6-yl)-prop-2-ynyl]-acetamide (0.90 g, 3.05 mmol) and 3-Methyl-4-(pyridin-3-yloxy)-phenylamine (0.61 g, 3.05 mmol) in tBuOH/DCE (5.0/5.0 mL) was refluxed under nitrogen for 40 minutes and concentrated. The residue was dissolved in MeOH (2.0 mL) and added to EtOAc with vigorous stirring to precipitate the HCI salt product as tan solid which was collected by vacuum-filtration, rinsed with EtOAc, and further dried to give 1.24 g (82%) of 2-Chloro-N-(3-{4-[3-methyl-4-(pyridin-3-yloxy)-phenylamino]-quinazolin-6-yl}-prop-2-ynyl)-acetamide: 1H NMR (CD3OD) δ 2.27 (s, 3H), 4.09 (s, 2H), 4.29 (s, 2H), 7.07 (d, 1H), 7.51 (m, 2H), 7.60 (d, 1H), 7.70 (s, 1H), 7.78 (d, 1H), 8.05 (d, 1H), 8.32 (m, 2H), 8.67 (s, 1H), 8.75 (s, 1H); MS m/z (MH+) 458.0.

後処理

  1. temperaturewas refluxed under nitrogen for 40 minutes
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in MeOH (2.0 mL)
  4. additionadded to EtOAc
  5. customto precipitate the HCI salt product as tan solid which
  6. filtrationwas collected by vacuum-filtration
  7. washrinsed with EtOAc
  8. customfurther dried

出典と根拠

ORDレコード
ord-e2f14231bc6147e7b44ee0b55bb6d6fc
出典データセット
uspto-grants-2005_05
特許番号
US06890924B2

反応ノート

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