Acetic Acid → HCID 11974119, 화합물

HRID 1826311노트

반응식

HRID 1826311 반응식
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:40][CH:41]([CH3:43])[CH3:42])=[CH:30][C:31]=3[O:33][CH:34]3[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]3)[N:26]=[CH:25][N:24]=2)=[C:20]2[O:44][CH2:45][O:46][C:19]2=[CH:18][CH:17]=1.C=O.C(O)(=O)C>CO.C(Cl)Cl>[Cl:15][C:16]1[C:21]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:40][CH:41]([CH3:42])[CH3:43])=[CH:30][C:31]=3[O:33][CH:34]3[CH2:35][CH2:36][N:37]([CH3:1])[CH2:38][CH2:39]3)[N:26]=[CH:25][N:24]=2)=[C:20]2[O:44][CH2:45][O:46][C:19]2=[CH:18][CH:17]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11974719HCID 11974719, 화합물

생성물 1

HCID 11974119HCID 11974119, 화합물수율 85.4%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Sodium triacetoxyborohydride (0.087 g) was added portionwise to a stirred mixture of 4-(6-chloro-2,3-methylenedioxyanilino)-7-isopropoxy-5-piperidin-4-yloxyquinazoline (0.125 g), aqueous formaldehyde (13N, 0.042 ml), acetic acid (0.019 ml), methylene chloride (5 ml) and methanol (2 ml) and the resultant mixture was heated to reflux for 3 minutes. The mixture was evaporated and the residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution. The organic layer was washed with brine, dried over magnesium sulphate and evaporated to give the title compound (0.11 g); NMR Spectrum: (CDCl3) 1.42 (d, 6H), 1.95–2.1 (m, 2H), 2.15–2.25 (m, 2H), 2.3 (s, 3H), 2.3–2.4 (m, 2H), 2.7–2.8 (m, 2H), 4.6 (m, 1H), 4.72 (m, 1H), 6.05 (s, 2H), 6.5 (d, 1H), 6.75 (d, 1H), 6.82 (d, 1H), 6.99 (d, 1H), 8.52 (s, 1H), 9.3 (s, 1H); Mass Spectrum: M+H+ 471 and 473.

후처리

  1. temperatureto reflux for 3 minutes
  2. customThe mixture was evaporated
  3. customthe residue was partitioned between ethyl acetate and 1N aqueous sodium hydroxide solution
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulphate
  6. customevaporated

출처 및 근거

ORD 기록
ord-da5a795beb7c4593b514a328310465e8
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049438B2

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