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Methoxyacetaldehyde → 6-Methoxy-7-(1-(2-methoxyethyl)piperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazoline

HRID 454071
ノート
印刷プレビュー

反応式

HRID 454071 の反応式
[CH3:1][O:2][CH2:3][CH:4]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][CH2:33][CH:34]1[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]1)[N:28]=[CH:27][N:26]=[C:25]2[O:40][C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[NH:46][C:45]([CH3:50])=[CH:44]2.C(=O)([O-])O.[Na+]>C(Cl)Cl.CO>[CH3:20][O:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[O:32][CH2:33][CH:34]1[CH2:39][CH2:38][N:37]([CH2:4][CH2:3][O:2][CH3:1])[CH2:36][CH2:35]1)[N:28]=[CH:27][N:26]=[C:25]2[O:40][C:41]1[CH:42]=[C:43]2[C:47](=[CH:48][CH:49]=1)[NH:46][C:45]([CH3:50])=[CH:44]2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 91563MethoxyacetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 220308736-Methoxy-4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline

生成物 1

HCID 220306856-Methoxy-7-(1-(2-methoxyethyl)piperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazoline収率 47.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Methoxyacetaldehyde (368 mg, 3.47 mol) (freshly distilled) followed by sodium triacetoxyborohydride (552 mg, 2.6 mol) were added to a solution of 6-methoxy-4-(2-methylindol-5-yloxy)-7-(piperidin-4-ylmethoxy)quinazoline (726 mg, 1.74 mmol), (prepared as described in Example 70), in a mixture of methylene chloride (15 ml) and methanol (15 ml). After stirring for 1.5 hours at ambient temperature, saturated sodium hydrogen carbonate was added. The volatiles were removed under vacuum and the residue was partitioned between methylene chloride and water. The organic layer, was separated, washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (80/20). After removal of the solvent, the residue was triturated with ether, collected by filtration, washed with ether and dried under vacuum at 60° C. to give 6-methoxy-7-(1-(2-methoxyethyl)piperidin-4-ylmethoxy)-4-(2-methylindol-5-yloxy)quinazoline (392 mg, 47%).

後処理

  1. customThe volatiles were removed under vacuum
  2. customthe residue was partitioned between methylene chloride and water
  3. customThe organic layer, was separated
  4. washwashed with water, brine
  5. dry with materialdried (MgSO4)
  6. customthe volatiles were removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/methanol (80/20)
  9. customAfter removal of the solvent
  10. customthe residue was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried under vacuum at 60° C.

出典と根拠

ORDレコード
ord-90e9a818006e49b8a64bdc1c6fee52e9
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492560B2

反応ノート

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