Morpholine → Spiro[2H-1,3-benzoxazine-2,4'-piperidin]-4(3H)-one

HRID 1639527

반응식

HRID 1639527 반응식
[NH:1]1[CH2:6][CH2:5][C:4](=[O:7])[CH2:3][CH2:2]1.C(N[C:12]1[CH:13]=[CH:14][C:15](O)=[C:16]([CH:20]=1)[C:17]([NH2:19])=[O:18])(=O)C.N1CCOCC1>CO.C(OCC)(=O)C>[NH:1]1[CH2:6][CH2:5][C:4]2([NH:19][C:17](=[O:18])[C:16]3[CH:20]=[CH:12][CH:13]=[CH:14][C:15]=3[O:7]2)[CH2:3][CH2:2]1

참가 물질

6

반응물 3

HCID 8083MorpholineHCID 337214-PiperidoneHCID 10330248Benzamide, 5-(acetylamino)-2-hydroxy-

생성물 1

HCID 379969Spiro[2H-1,3-benzoxazine-2,4'-piperidin]-4(3H)-one

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 24 mg (0.077 mmol) of N-[4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone, 15 mg (0.077 mmol) of 5-acetamido-2-hydroxybenzamide, and 0.020 mL of morpholine in 3 mL of methanol is refluxed for 48 hr. The reaction mixture is diluted with ethyl acetate, and washed with water, brine, and dried over Na2SO4. After solvent removal by rotoevaporation, the crude product is purified by preparative TLC to give 11 mg (0.022 mmol, 30% yield) of 6-acetamido-1′-[4,8-dimethoxyquinoline-2-yl)carbonyl]spiro[2H-1,3-benzoxazin-2,4′-piperidin]-4-(3H)-one (Compound 9): 1H NMR (DMSO-d6): δ 2.02 (s, 3H), 3.95 (s, 3H), 4.06 (s, 3H), 7.03 (d, 1H), 8.19 (s, 1H), 7.24 (d of d, 1H), 7.52 (d of d, 1H), 7.67 (m, 2H), 8.02 (d, 1H), 8.82, (s, 1H) and 9.98 ppm (s, 1H). MS m/z: 491.1 (M+H)+, 513.2 (M+Na)+.

후처리

  1. temperatureis refluxed for 48 hr
  2. washwashed with water, brine
  3. dry with materialdried over Na2SO4
  4. customAfter solvent removal by rotoevaporation
  5. customthe crude product is purified by preparative TLC

출처 및 근거

ORD 기록
ord-764a21ddb1184ccebf879e23a3e47f8b
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08110570B2

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