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

HRID 1426163

반응식

HRID 1426163 반응식
[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

참가 물질

4

반응물 2

HCID 206265543-(Benzyloxy)-5-bromopyridin-2-amineHCID 86639699HCID 86639699, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-85f317336324411c9ac02459e4189941
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08933077B2

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