4-Chloroaniline → HCID 57681184, compound

HRID 1896684Notes

Reaction equation

HRID 1896684 reaction equation
C(N(CC)C(C)C)(C)C.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[N:34]1[CH:39]=[CH:38][C:37]([CH:40]([S:42][C:43]2[C:48]([C:49]([OH:51])=O)=[CH:47][CH:46]=[CH:45][N:44]=2)[CH3:41])=[CH:36][CH:35]=1.[Cl:52][C:53]1[CH:59]=[CH:58][C:56]([NH2:57])=[CH:55][CH:54]=1>CN(C)C=O.C(OCC)(=O)C>[Cl:52][C:53]1[CH:59]=[CH:58][C:56]([NH:57][C:49]([C:48]2[C:43]([S:42][CH:40]([C:37]3[CH:36]=[CH:35][N:34]=[CH:39][CH:38]=3)[CH3:41])=[N:44][CH:45]=[CH:46][CH:47]=2)=[O:51])=[CH:55][CH:54]=1

Participants

7

Reactant 4

HCID 78124-ChloroanilineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 23093832HCID 23093832, compound

Product 1

HCID 57681184HCID 57681184, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

N,N-Diisopropylethylamine (0.29 mL, 1.7 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N′, N′-tetramethyluronium hexafluorophosphate (330 mg, 0.87 mmol) were added to a solution of 2-[1-(4-pyridyl)ethylthio]pyridine-3-carboxylic acid (200 mg, 0.77 mmol, Reference compound No. 5-1) and 4-chloroaniline (110 mg, 0.85 mmol) in N,N-dimethylformamide (2.0 mL), then the mixture was stirred at room temperature for 13 hours. Ethyl acetate (30 mL) was added to the reaction mixture, the ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (30 mL) twice and brine (30 mL) twice, then dried over anhydrous magnesium sulfate. The resulting residue by evaporated under reduced pressure was purified by silica gel column chromatography to give 41 mg of the target compound as a colorless solid. (Yield 14%)

Workup

  1. washthe ethyl acetate layer was washed with a saturated aqueous sodium hydrogencarbonate solution (30 mL) twice
  2. dry with materialbrine (30 mL) twice, then dried over anhydrous magnesium sulfate
  3. customThe resulting residue by evaporated under reduced pressure
  4. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-96bf3466ba9e404ab7b853fba560ca7d
Source dataset
uspto-grants-2013_08
Patent number
US08518973B2

Reaction notes

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