4-Methylmorpholine → N-(Benzyloxy)-4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzamide

HRID 1061296

反応式

HRID 1061296 の反応式
[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([C:11]3[CH:19]=[CH:18][C:14]([C:15]([OH:17])=O)=[CH:13][CH:12]=3)[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.Cl.CN(C)CCCN=C=NCC.Cl.[CH2:33]([O:40][NH2:41])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.CN1CCOCC1>C(Cl)Cl>[CH2:33]([O:40][NH:41][C:15](=[O:17])[C:14]1[CH:13]=[CH:12][C:11]([N:8]2[CH2:7][CH2:6][C:5]3([O:4][CH2:3][CH2:2][O:1]3)[CH2:10][CH2:9]2)=[CH:19][CH:18]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 102312Benzyloxyamine hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 159484254-(1,4-Dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid

生成物 1

HCID 22220505N-(Benzyloxy)-4-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)benzamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-(1,4-dioxa-8-aza-spiro[4.5]dec-8-yl)-benzoic acid (which was obtained in Example 150) (1.58 g, 6 mmol), 1-[3-(dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (1.34 g, 7 mmol) and O-benzylhydroxyamine hydrochloride (1.05 g, 6.6 mmol) was stirred in methylene chloride (150 mL). N-methylmorpholine (1.82 g, 18 mol) was added dropwise and the mixture was stirred overnight. The mixture was then washed with 0.05 N hydrochloric acid and water. The resulting solution was dried with magnesium sulfate and concentrated. The residue was crystallized from methylene chloride/hexanes to give the title compound as a white solid; 1H NMR (300 MHz, CDCl3) δ 1.67 (t, J=5.6 Hz, 4H), 3.42 (t, J=5.6 Hz, 4H), 3.91 (s, 4H), 4.89 (s, 2H), 6.97 (d, J=9.0 Hz, 2H), 7.30-7.50 (m, 5H), 7.62 (d, J=9.0 Hz, 2H); MS (ES) m/z: 369.3 (MH+); HRMS Calcd. for C21H24N2O4 (M+): 368.1736. Found: 368.1744.

後処理

  1. washThe mixture was then washed with 0.05 N hydrochloric acid and water
  2. dry with materialThe resulting solution was dried with magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was crystallized from methylene chloride/hexanes

出典と根拠

ORDレコード
ord-5b85741605d248d4bfb1ea49fd1ec0aa
出典データセット
uspto-grants-2003_02
特許番号
US06525202B2

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