Pyridine → HCID 73505016, compound

HRID 590826Notes

Reaction equation

HRID 590826 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 73505016HCID 73505016, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-2e38955b907c467d8e7c2f22fe653bf1
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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