2-Amino-5-hydroxypyridine → HCID 90411099、化合物

HRID 626587ノート

反応式

HRID 626587 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 90411099HCID 90411099、化合物収率 57.1%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 31374Dimethylacetamide溶媒2 回

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-2ab53b27fbfe49faab008a51ec2bec12
出典データセット
uspto-grants-2016_04
特許番号
US09309224B2

反応ノート

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