4-Tert-Butylaniline → HCID 86588706, compound

HRID 1786379Notes

Reaction equation

HRID 1786379 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([Cl:11])=[CH:6][C:7]=1[C:8](O)=[O:9].[C:12]([C:16]1[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=1)([CH3:15])([CH3:14])[CH3:13].CN(C([O:30][N:31]1[N:39]=[N:38][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][C:32]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[C:12]([C:16]1[CH:17]=[CH:18][C:19]([NH:20][C:8]([C:7]2[CH:6]=[C:5]([Cl:11])[N:4]=[N:3][C:2]=2[O:30][N:31]2[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[N:38]=[N:39]2)=[O:9])=[CH:21][CH:22]=1)([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 4

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 4338043,6-Dichloropyridazine-4-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 86588706HCID 86588706, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 3,6-dichloropyridazine-4-carboxylic acid (1.00 g, 5.18 mmol), 4-tert-butylaniline (0.92 ml, 5.60 mmol), TBTU (1.75 g, 5.44 mmol), and DIEA (1.80 ml, 10.4 mmol) in 7.5 ml of anhydrous DMF was stirred at RT under N2 overnight. The mixtrue was diluted with H2O, extracted with EtOAc, and the combined organic portions were washed with brine, dried with Na2SO4, filtered, and condensed. The crude compound was purified by flash column chromatography (hexanes/EtOAc/CH2Cl2, 9:0:1 to 7:2:1), to provide the desired compound as a light yellowish solid. MS (ES+): 423.0 (M+H)+. Calc'd for C21H19ClN6O2—422.87.

Workup

  1. extractionextracted with EtOAc
  2. washthe combined organic portions were washed with brine
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. customcondensed
  6. customThe crude compound was purified by flash column chromatography (hexanes/EtOAc/CH2Cl2, 9:0:1 to 7:2:1)

Sources & evidence

ORD record
ord-cf7b1f854a70487c9d09d1b2da244b25
Source dataset
uspto-grants-2009_03
Patent number
US07507748B2

Reaction notes

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