3-(Benzyloxy)-5-bromopyridin-2-amine → Methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate

HRID 1426163

反応式

HRID 1426163 の反応式
[CH2:1]([O:8][C:9]1[C:10]([NH2:16])=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:18]1[C:27]([N:28]=[C:29]=[S:30])=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[C:10]([NH:16][C:29]2[S:30][C:18]3[C:27]([N:28]=2)=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][N:19]=3)=[N:11][CH:12]=[C:13]([Br:15])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 206265543-(Benzyloxy)-5-bromopyridin-2-amineHCID 86639699HCID 86639699、化合物

生成物 1

HCID 59225690Methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate収率 69.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
80 °C

実験手順

3-(Benzyloxy)-5-bromopyridin-2-amine (1.50 g, 5.37 mmol) was added to a mixture of methyl 6-chloro-5-isothiocyanatonicotinate (1.23 g, 5.37 mmol) in DMF (4 mL). The reaction mixture was stirred at 80° C. for an hour, then at 110° C. for 2 hours. The reaction mixture was cooled, partitioned between dichloromethane (200 mL) and water (200 mL) and 2N NaOH (15 mL). The organic layer was washed with water and brine, dried, and concentrated. The residue was dissolved in warm dichloromethane (70 mL), and to this was added warm hexanes (40° C.) (250 mL). The solution was cooled to ambient temperature and the resulting solids were collected by filtration to afford methyl 2-(3-(benzyloxy)-5-bromopyridin-2-ylamino)thiazolo[5,4-b]pyridine-6-carboxylate (1.77 g, 69.9% yield) as a white powder. 1H NMR (CDCl3) δ 3.98 (s, 3H), 5.15 (s, 2H), 7.35 (s, 1H), 7.46 (m, 5H), 8.10 (s, 1H), 8.42 (s, 1H), 8.76 (bs, 1H), 9.02 (s, 1H).

後処理

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between dichloromethane (200 mL) and water (200 mL) and 2N NaOH (15 mL)
  3. washThe organic layer was washed with water and brine
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in warm dichloromethane (70 mL)
  7. additionto this was added
  8. temperaturewarm hexanes (40° C.) (250 mL)
  9. temperatureThe solution was cooled to ambient temperature
  10. filtrationthe resulting solids were collected by filtration

出典と根拠

ORDレコード
ord-85f317336324411c9ac02459e4189941
出典データセット
uspto-grants-2015_01
特許番号
US08933077B2

関連ノート

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