2-Amino-5-hydroxypyridine → HCID 90411099, 화합물

HRID 626587노트

반응식

HRID 626587 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][N:3]=1.CC(C)([O-])C.[K+].Cl[C:16]1[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH:25]2[CH2:27][CH2:26]2)=[O:23])[CH:17]=1>CC(N(C)C)=O.CCOC(C)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([O:8][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]([NH:24][CH:25]3[CH2:26][CH2:27]3)=[O:23])[CH:17]=2)=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 42319722-Amino-5-hydroxypyridineHCID 23665647Potassium tert-butoxideHCID 256064754-Chloro-N-cyclopropylpyridine-2-carboxamide

생성물 1

HCID 90411099HCID 90411099, 화합물수율 57.1%

시약·촉매·용매 2

HCID 8857Ethyl Acetate용매HCID 31374Dimethylacetamide용매2회

실험 절차

A solution of 2-amino-5-hydroxypyridine (0.578 g, 5.25 mmol) in DMA (8.75 mL) was treated with potassium tert-butoxide (0.663 g, 5.90 mmol), stirred at RT for 1 h, treated with a solution of 4-chloro-N-cyclopropylpicolinamide (0.86 g, 4.37 mmol) in DMA (8.75 mL) and stirred at RT for 20 h. The mixture was diluted with EtOAc, washed with 1N NaOH, then brine and the organic layer was dried over Na2SO4, concentrated to dryness and purified by silica gel chromatography (MeOH/EtOAc) to afford 4-((6-aminopyridin-3-yl)oxy)-N-cyclopropylpicolinamide (0.674 g, 57%). 1H NMR (400 MHz, DMSO-d6): δ 8.72 (d, J=5.0 Hz, 1H), 8.44 (d, J=5.6 Hz, 1H), 7.82 (d, J=2.9 Hz, 1H), 7.31-7.30 (m, 2H), 7.11 (dd, J=5.6, 2.6 Hz, 1H), 6.53 (d, J=8.9 Hz, 1H), 6.08 (s, 2H), 2.85-2.84 (m, 1H), 0.65-0.62 (m, 4H); MS (ESI) m/z: 271.1 (M+H+).

후처리

  1. stirringstirred at RT for 20 h
  2. washwashed with 1N NaOH
  3. dry with materialbrine and the organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. custompurified by silica gel chromatography (MeOH/EtOAc)

출처 및 근거

ORD 기록
ord-2ab53b27fbfe49faab008a51ec2bec12
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309224B2

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