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Morpholine → 2-Methoxy-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester

HRID 1753877
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HRID 1753877 반응식
[CH3:1][O:2][C:3]([C:5]1[C:6]([O:13][CH3:14])=[N:7][C:8](Cl)=[CH:9][C:10]=1[CH3:11])=[O:4].[NH:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1.CCN(CC)CC.CCOC(C)=O>CN1C(=O)CCC1>[CH3:1][O:2][C:3]([C:5]1[C:6]([O:13][CH3:14])=[N:7][C:8]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=[CH:9][C:10]=1[CH3:11])=[O:4]
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참가 물질

6

반응물 4

HCID 8083MorpholineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 57441127Methyl 6-chloro-2-methoxy-4-methylnicotinate

생성물 1

HCID 866643212-Methoxy-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester수율 45%

시약·촉매·용매 1

HCID 13387
N-methyl-2-pyrrolidone
용매

실험 절차

A solution of 5.0 g (21.8 mmol) 6-chloro-2-methoxy-4-methylpyridine-3-carboxylic acid methylester, 2.0 g (24.0 mmol) morpholine and 6.0 ml (43.5 mmol) NEt3 in NMP (21 ml) was heated at 90° C. for 2 d. After cooling to RT the mixture was partiotionated between EtOAc and a 1M aq. NaHCO3 sol. The organic layer was separated, dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 4:1) provided 2.7 g (9.8 mmol, 45%) 2-methoxy-4-methyl-6-morpholino-pyridine-3-carboxylic acid methylester.

후처리

  1. customa 1M aq. NaHCO3 sol. The organic layer was separated
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by CC (hexane/EtOAc 4:1)

출처 및 근거

ORD 기록
ord-bdef43dc9143456dbdca893e1d84c827
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09168259B2

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