3,5-Dimethylaniline → HCID 11964856, compound

HRID 1890500Notes

Reaction equation

HRID 1890500 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][S:9][C:10]2[N:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]1[CH:21]=[C:22]([CH:24]=[C:25]([CH3:27])[CH:26]=1)[NH2:23].C(N(CC)C(C)C)(C)C.C(OCC)(=O)C>CN(C)C=O>[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][S:9][C:10]2[C:11]([C:12]([NH:23][C:22]3[CH:24]=[C:25]([CH3:27])[CH:26]=[C:20]([CH3:19])[CH:21]=3)=[O:14])=[CH:15][CH:16]=[CH:17][N:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 79493,5-DimethylanilineHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 57971149HCID 57971149, compound

Product 1

HCID 11964856HCID 11964856, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(7-Azabenzotriazole-1-yl)-N,N,N′,N′-tetrauroniumhexafluorophosphate (110 mg, 0.29 mmol) was added to a solution of 2-(2-aminopyrimidin-4-ylmethylthio)nicotinic acid (60 mg, 0.24 mmol, Reference Compound No. 12-1), 3,5-dimethylaniline (33 μL, 0.27 mmol) and N,N-diisopropylethylamine (0.93 μL, 0.53 mmol) in anhydrous N,N-dimethylformamide (1.0 mL) at room temperature, and the mixture was stirred for 18 hours. Ethyl acetate (30 mL) was added thereto, and then the whole was washed with saturated aqueous sodium hydrogencarbonate solution (50 mL) and brine (50 mL), then the organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, the precipitated solid was filtered off, and washed with 50% diethylether-ethyl acetate solution. The solid was then dried at 60° C. under reduced pressure to give 35 mg of the target compound as a light brown solid (Yield: 41%).

Workup

  1. washthe whole was washed with saturated aqueous sodium hydrogencarbonate solution (50 mL) and brine (50 mL)
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. filtrationthe precipitated solid was filtered off
  5. washwashed with 50% diethylether-ethyl acetate solution
  6. customThe solid was then dried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-83acc9a3c6e34fd78668ff44b88cf213
Source dataset
uspto-grants-2013_08
Patent number
US08507485B2

Reaction notes

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