HCID 86697750, compound → 3-Amino-6-[1-(3-hydroxypropyl)-3-methyl-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamide

HRID 2279809Notes

Reaction equation

HRID 2279809 reaction equation
[NH2:1][C:2]1[C:3]([C:25]([NH:27][CH3:28])=[O:26])=[N:4][C:5]([C:8]2[C:9]([CH3:24])=[N:10][N:11]([CH2:13][CH2:14][CH2:15][O:16]CC3C=CC=CC=3)[CH:12]=2)=[CH:6][CH:7]=1>CCO.[Pd]>[NH2:1][C:2]1[C:3]([C:25]([NH:27][CH3:28])=[O:26])=[N:4][C:5]([C:8]2[C:9]([CH3:24])=[N:10][N:11]([CH2:13][CH2:14][CH2:15][OH:16])[CH:12]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86697750HCID 86697750, compound2×

Product 1

HCID 866977493-Amino-6-[1-(3-hydroxypropyl)-3-methyl-1H-pyrazol-4-yl]-N-methylpyridine-2-carboxamideYield 70.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-Amino-6-{1-[3-(benzyloxy)propyl]-3-methyl-1H-pyrazol-4-yl}-N-methylpyridine-2-carboxamide (Compound 34D, 639 mg, 1.68 mmol) in EtOH (18.0 mL) and palladium on carbon (10:90, Palladium 10% wt. on Calcium Carbonate:carbon black, 100.0 mg, 0.048 mmol) was evacuated and flushed with argon (3×). After a fourth evacuation, the mixture was flushed with H2 and allowed to stir overnight at rt. The reaction mixture was filtered, concentrated in vacuo and purified using a Teledyne ISCO Combiflash® Rf system [elution gradient: 0→10% MeOH in DCM] to afford 342 mg of the title compound (70%). 1H NMR (400 MHz, CDCl3) δ 8.01 (s, 1H), 7.42 (d, J=8.6 Hz, 1H), 7.16 (d, J=8.6 Hz, 1H), 4.19 (t, J=7.0 Hz, 2H), 3.55 (t, J=6.2 Hz, 2H), 2.94 (s, 3H), 2.48 (s, 3H), 2.05 (t, J=6.4 Hz, 2H). MS (ESI): m/z=290.58 [M+H]+. UPLC: tR=0.65 min (UPLC-SQD: analytical—2 min).

Workup

  1. customwas evacuated
  2. customflushed with argon (3×)
  3. customAfter a fourth evacuation, the mixture was flushed with H2
  4. filtrationThe reaction mixture was filtered
  5. concentrationconcentrated in vacuo
  6. custompurified
  7. washa Teledyne ISCO Combiflash® Rf system [elution gradient: 0→10% MeOH in DCM]

Sources & evidence

ORD record
ord-69915ba1b9fa4ce2bd82d80d90b8e5b9
Source dataset
uspto-grants-2015_09
Patent number
US09133224B2

Reaction notes

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