1-Hydroxybenzotriazole → 3-methyl-N-[3-({2-[(morpholin-4-ylacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]pyridine-2-carboxamide

HRID 1874539노트

반응식

HRID 1874539 반응식
[NH2:1][C:2]1[N:3]=[C:4]2[CH:9]=[CH:8][C:7]([O:10][C:11]3[CH:12]=[C:13]([NH:17][C:18]([C:20]4[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][N:21]=4)=[O:19])[CH:14]=[CH:15][CH:16]=3)=[CH:6][N:5]2[CH:27]=1.[N:28]1([CH2:34][C:35](O)=[O:36])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.Cl.CN(C)CCCN=C=NCC.N1(O)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>C(=O)([O-])O.[Na+].CN(C)C(=O)C>[CH3:26][C:25]1[C:20]([C:18]([NH:17][C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([O:10][C:7]3[CH:8]=[CH:9][C:4]4[N:5]([CH:27]=[C:2]([NH:1][C:35](=[O:36])[CH2:34][N:28]5[CH2:33][CH2:32][O:31][CH2:30][CH2:29]5)[N:3]=4)[CH:6]=3)[CH:12]=2)=[O:19])=[N:21][CH:22]=[CH:23][CH:24]=1

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 4389684-Morpholineacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57749390N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide

생성물 1

HCID 577493753-methyl-N-[3-({2-[(morpholin-4-ylacetyl)amino]imidazo[1,2-a]pyridin-6-yl}oxy)phenyl]pyridine-2-carboxamide수율 47.4%

시약·촉매·용매 2

HCID 31374Dimethylacetamide용매HCID 516892Sodium Bicarbonate용매

실험 절차

A mixture of N-{3-[(2-aminoimidazo[1,2-a]pyridin-6-yl)oxy]phenyl}-3-methylpyridine-2-carboxamide (129 mg, 0.359 mmol), morpholin-4-ylacetic acid (56.8 mg, 0.391 mmol), N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride (97.8 mg, 0.510 mmol), 1H-benzotriazol-1-ol (50.7 mg, 0.375 mmol), N,N-diisopropylethylamine (123 μL, 0.719 mmol) and N,N-dimethylacetamide (5 mL) was stirred at room temperature for 21 hr. The reaction mixture was diluted with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (NH silica gel, 0%→75% ethyl acetate-hexane) to give the title compound (82.8 mg, 47%) as a pale-yellow solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (NH silica gel, 0%→75% ethyl acetate-hexane)

출처 및 근거

ORD 기록
ord-f679f7eb47d84fd996fa64980340ec0a
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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