Pyridine → HCID 58717209, compound

HRID 1244538Notes

Reaction equation

HRID 1244538 reaction equation
CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH3:12][N:13]([C:15](=[N:43][S:44]([CH3:47])(=[O:46])=[O:45])[C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][C:25]3[C:28]([C:39]([NH2:41])=O)=[N:29][N:30]([C:31]4[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=4)[C:24]=3[C:23]2=[O:42])=[CH:18][CH:17]=1)[CH3:14].N1C=CC=CC=1>C(#N)C>[C:39]([C:28]1[C:25]2[CH2:26][CH2:27][N:22]([C:19]3[CH:20]=[CH:21][C:16]([C:15]([N:13]([CH3:14])[CH3:12])=[N:43][S:44]([CH3:47])(=[O:46])=[O:45])=[CH:17][CH:18]=3)[C:23](=[O:42])[C:24]=2[N:30]([C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)[N:29]=1)#[N:41]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 58717241HCID 58717241, compound

Product 1

HCID 58717209HCID 58717209, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

N,N-Dimethylformamide (0.1 mL) was added to acetonitrile (10 mL) and cooled to 0° C. Oxalyl chloride (0.113 mL, 1.29 mmol) was added to the reaction. Once gas evolution stopped, 6-[4-(dimethylamino-methanesulfonylimino-methyl)-phenyl]-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid amide (0.020 g, 0.039 mmol) was dissolved in acetonitrile (2 mL) and added to the reaction and stirred at 0° C. for 20 min. Pyridine (1 mL) was then added to the reaction, and it was warmed to rt and stirred overnight. The reaction was quenched with 1N hydrogen chloride (50 mL), extracted with ether 3×50 mL), washed with brine (1×50 mL), dried with MgSO4, and concentrated. Purification by reverse phase HPLC and freeze-dried to afford the title compound (0.014 g, 72%): 1H NMR (CHCl3) δ 7.45 (d, j=8.8 Hz, 2H), 7.40 (d, j=1.1 Hz, 4H), 6.95 (d, j=8.7 Hz, 2H), 4.21 (t, j=6.6 Hz, 2H), 3.83 (s, 3H), 3.19 (s, 3H), 3.17 (t, j=6.1 Hz, 2H), 2.94 (s, 3H), 2.81 (s, 3H) ppm; Mass Spec 493.5 (M+H)+.

Workup

  1. additionadded to the reaction
  2. temperaturewas warmed to rt
  3. stirringstirred overnight
  4. customThe reaction was quenched with 1N hydrogen chloride (50 mL)
  5. extractionextracted with ether 3×50 mL),
  6. washwashed with brine (1×50 mL)
  7. dry with materialdried with MgSO4
  8. concentrationconcentrated
  9. customPurification by reverse phase HPLC
  10. customfreeze-dried

Sources & evidence

ORD record
ord-e36ec6cd5b8e4e698ada1d41ff64daba
Source dataset
uspto-grants-2006_10
Patent number
US07122557B2

Reaction notes

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