Propylamine → HCID 23093755, compound

HRID 1896686Notes

Reaction equation

HRID 1896686 reaction equation
C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.[N:17]1(OC(N(C)C)=[N+](C)C)[C:21]2N=CC=[CH:25][C:20]=2N=N1.[C:34]([C:37]1[CH:42]=[C:41]([CH2:43][S:44][C:45]2[C:50]([C:51]([NH:53][C:54]3[CH:59]=[C:58]([CH3:60])[CH:57]=[C:56]([CH3:61])[CH:55]=3)=[O:52])=[CH:49][CH:48]=[CH:47][N:46]=2)[CH:40]=[CH:39][N:38]=1)(O)=[O:35].C(N)CC>CN(C)C=O.C(OCC)(=O)C>[CH3:60][C:58]1[CH:59]=[C:54]([NH:53][C:51]([C:50]2[C:45]([S:44][CH2:43][C:41]3[CH:40]=[CH:39][N:38]=[C:37]([C:34]([NH:17][CH2:21][CH2:20][CH3:25])=[O:35])[CH:42]=3)=[N:46][CH:47]=[CH:48][CH:49]=2)=[O:52])[CH:55]=[C:56]([CH3:61])[CH:57]=1

Participants

7

Reactant 4

HCID 7852PropylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23093762HCID 23093762, compound

Product 1

HCID 23093755HCID 23093755, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

N,N-Diisopropylethylamine (40 μL, 0.23 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (51 mg, 0.14 mmol) were added to a solution of 2-(2-carboxypyridine-4-ylmethylthio)-N-(3,5-dimethylphenyl)pyridine-3-carboxamide (42 mg, 0.11 mmol, Compound No. 6-1) and n-propylamine (34 μL, 0.41 mmol) in N,N-dimethylformamide (1 mL) at room temperature, this mixture was stirred at 40° C. for 3 hours. The reaction mixture was diluted with ethyl acetate (20 mL), then the ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (40 mL) and brine (30 mL) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was washed with diethyl ether. This solid was dried at 50° C. under reduced pressure to give 21 mg of the target compound as a white solid. (Yield 46%)

Workup

  1. washthe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (40 mL) and brine (30 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washthe resulting residue was washed with diethyl ether
  5. customThis solid was dried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-5b8600826c7d4bc19572e254a580d6ed
Source dataset
uspto-grants-2013_08
Patent number
US08518973B2

Reaction notes

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