Pyridinium chloride → 4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-ol

HRID 1162214ノート

反応式

HRID 1162214 の反応式
C[O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([NH:13][C:14]1[CH:15]=[C:16]3[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)[N:18]=[CH:17]3)=[N:6][CH:7]=[N:8]2.Cl.N1C=CC=CC=1>N1C=CC=CC=1>[N:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH2:23][N:19]1[C:20]2[C:16](=[CH:15][C:14]([NH:13][C:5]3[C:4]4[C:3]([OH:2])=[CH:12][CH:11]=[CH:10][C:9]=4[N:8]=[CH:7][N:6]=3)=[CH:22][CH:21]=2)[CH:17]=[N:18]1

参加物

4

反応物 2

HCID 10176127Pyridinium chlorideHCID 686187925-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine

生成物 1

HCID 1363467194-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-ol収率 100.1%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A mixture of 5-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine (10.1 g, 27.4 mmol) and pyridine hydrochloride (15.8 g, 137 mmol) in pyridine (150 ml) was heated at reflux for 3 hours. After cooling and evaporation of the solvents, the residue was triturated in 5% aqueous sodium bicarbonate and the resulting mixture was stirred for 30 minutes. The yellowish precipitate was filtered, washed with water and ether, and dried over P2O5 under high vacuum to give 4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-ol as a solid (10.1 g, 100%); NMR spectrum 5.76 (s, 2H), 6.67 (m, 2H), 6.96 (d, 1H), 7.29 (m, 1H), 7.42 (m, 1H), 7.52 (dd, 1H), 7.74-7.66 (m, 2H), 8.13 (s, 1H), 8.33 (s, 2H), 8.52 (d, 1H); Mass spectrum MH+ 369.

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. temperatureAfter cooling
  4. customevaporation of the solvents
  5. customthe residue was triturated in 5% aqueous sodium bicarbonate
  6. filtrationThe yellowish precipitate was filtered
  7. washwashed with water and ether
  8. dry with materialdried over P2O5 under high vacuum

出典と根拠

ORDレコード
ord-0dc5c2fc1e21469b9b7b905462872429
出典データセット
uspto-grants-2010_10
特許番号
US07820683B2

反応ノート

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