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Acetic Acid → methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

HRID 1399787
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HRID 1399787 반응식
[NH2:1][C:2]1[C:3]([NH2:18])=[C:4]([CH:9]=[C:10]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:19][C:20](O)=O>>[CH3:19][C:20]1[NH:1][C:2]2=[N:11][C:10]([N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[C:3]2[N:18]=1
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참가 물질

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반응물 2

HCID 176Acetic AcidHCID 89647670Methyl 2,3-diamino-6-morpholinoisonicotinate2회

생성물 1

HCID 178498376methyl 2-methyl-5-morpholino-3H-imidazo[4,5-b]pyridine-7-carboxylate

실험 절차

A solution of methyl 2,3-diamino-6-morpholinoisonicotinate (4.3 g, 17 mmol) in CH3COOH (100 mL) was refluxed for 16 h. LCMS showed no methyl 2,3-diamino-6-morpholinoisonicotinate left and the desired product formed. It was cooled to room temperature and the solvent was removed in vacuo. The residue was then purified by chromatography on silica gel eluted with MeOH/DCM=1/50 to afford the desired product as a black solid (1.07 g, 23%); LC/MS: MS (ES+) m/e 277 (MH+); 1H NMR (300 MHz, CDCl3) δ ppm 2.69 (s, 3H), 3.58 (t, J=4.8 Hz, 4H), 3.86 (t, J=4.8 Hz, 4H), 4.02 (s, 3H), 7.12 (s, 1H).

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출처 및 근거

ORD 기록
ord-f461234f0c7049f1ab344eeb3c60664c
출처 데이터셋
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08906910B2

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