Ammonia → HCID 135510689, 화합물

HRID 641744

반응식

HRID 641744 반응식
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]

참가 물질

7

반응물 5

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

생성물 1

HCID 135510689HCID 135510689, 화합물수율 62.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

반응 조건

온도
5 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-26a785309f7744ef9183820051903752
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696214B2

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