Ammonia → HCID 135510689、化合物

HRID 641744

反応式

HRID 641744 の反応式
N(C(OC(C)(C)C)=O)=NC([O-])=O.[OH:13][C:14]1[C:23]([O:24][CH3:25])=[CH:22][CH:21]=[C:20]2[C:15]=1[C:16](=[O:34])[N:17](COC(=O)C(C)(C)C)[CH:18]=[N:19]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:55]1[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]1.N>C(Cl)Cl>[CH3:25][O:24][C:23]1[C:14]([O:13][CH:55]2[CH2:60][CH2:59][N:58]([CH3:61])[CH2:57][CH2:56]2)=[C:15]2[C:20](=[CH:21][CH:22]=1)[N:19]=[CH:18][NH:17][C:16]2=[O:34]

参加物

7

反応物 5

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 660484-Piperidinol, 1-methyl-HCID 11974824HCID 11974824、化合物HCID 86609045Tert-butyl azodicarboxylate

生成物 1

HCID 135510689HCID 135510689、化合物収率 62.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
5 °C

実験手順

A solution of di-(tert-butyl azodicarboxylate (1.75 g) in methylene chloride (3 ml) was added to a stirred mixture of 5-hydroxy-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one (1.55 g), triphenylphosphine (1.99 g), 4-hydroxy-1-methylpiperidine (0.75 g) and methylene chloride (12 ml) which had been cooled to 5° C. The mixture was stirred at ambient temperature for 1 hour. The mixture was evaporated and the residue was purified by column chromatography on silica using a 9:10:1 mixture of methylene chloride, ethyl acetate and a saturated methanolic ammonia solution as eluent. The material so obtained was stirred in a saturated methanolic ammonia solution for 48 hours. The mixture was evaporated and the residue was triturated under diethyl ether. The resultant solid was washed with diethyl ether and dried under vacuum to give 6-methoxy-5-(N-methylpiperidin-4-yloxy)-3,4-dihydroquinazolin-4-one (0.92 g); NMR Spectrum: (DMSOd6) 1.7-1.9 (m, 4H), 1.95 (t, 2H), 2.15 (s, 3H), 2.7 (m, 2H), 3.85 (s, 3H), 4.08 (m, 1H), 7.4 (d, 1H), 7.6 (d, 1H), 7.85 (s, 1H), 11.8 (br s, 1H); Mass Spectrum: M+H+ 290.

後処理

  1. customThe mixture was evaporated
  2. customthe residue was purified by column chromatography on silica using
  3. additiona 9:10:1 mixture of methylene chloride, ethyl acetate
  4. customThe material so obtained
  5. customThe mixture was evaporated
  6. customthe residue was triturated under diethyl ether
  7. washThe resultant solid was washed with diethyl ether
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-26a785309f7744ef9183820051903752
出典データセット
uspto-grants-2010_04
特許番号
US07696214B2

関連ノート

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