Pyridine → HCID 73505016, 화합물

HRID 590826노트

반응식

HRID 590826 반응식
[NH2:1][C:2]1[C:6]2[C:7]([CH2:23][O:24][CH3:25])=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[NH:4][N:3]=1.N1C=CC=CC=1.[C:32](Cl)([CH3:34])=[O:33].[OH-].[Na+]>C1COCC1>[CH3:25][O:24][CH2:23][C:7]1[C:6]2[C:2]([NH:1][C:32](=[O:33])[CH3:34])=[N:3][NH:4][C:5]=2[CH:10]=[C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])=[O:13])[N:8]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 73505014HCID 73505014, 화합물

생성물 1

HCID 73505016HCID 73505016, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (R)-1-(3-amino-4-(methoxymethyl)-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (30 mg, 0.088 mmol) in THF (1 ml) was charged with pyridine (72 μl, 0.890 mmol) and AcCl (62 μl, 0.872 mmol). The mixture was stirred at RT for 17 hr before 1N NaOH (1.2 ml, 1.200 mmol) was added and stirred at RT for 2 hr and then heated to 50° C. for 1 hr. The reaction was quenched with sat aq NH4Cl and extracted into EtOAc. The mixture was washed with sat aq NH4Cl followed by brine, dried over MgSO4, filtered, concentrated in vacuo and purified via flash chromatography (0-20% MeOH/DCM) to give (R)—N-(4-(methoxymethyl)-6-(3-(1-phenylethyl)ureido)-1H-pyrazolo[4,3-c]pyridin-3-yl)acetamide. MS ESI calc'd for C19H23N6O3 [M+H]+ 383. found 383. 1H NMR (ppm, 500 MHz, DMSO-d6) δ 12.81 (s, 1H), 10.01 (s, 1H), 9.13 (s, 1H), 7.33 (m, 5H), 7.22 (m, 1H), 4.89 (t, J=6.8 Hz), 4.59 (s, 2H), 3.28 (s, 3H), 2.06 (s, 3H), 1.39 (d, 5.1 Hz).

후처리

  1. additionwas added
  2. temperatureheated to 50° C. for 1 hr
  3. customThe reaction was quenched with sat aq NH4Cl
  4. extractionextracted into EtOAc
  5. washThe mixture was washed with sat aq NH4Cl
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. custompurified via flash chromatography (0-20% MeOH/DCM)

출처 및 근거

ORD 기록
ord-2e38955b907c467d8e7c2f22fe653bf1
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09233979B2

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