4-Tert-Butylaniline → HCID 11472986, compound

HRID 1822914Notes

Reaction equation

HRID 1822914 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=1.CCN(C(C)C)C(C)C.[C:25]([C:29]1[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=1)([CH3:28])([CH3:27])[CH3:26]>O=S(Cl)Cl>[C:25]([C:29]1[CH:30]=[CH:31][C:32]([NH:33][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)=[CH:15][CH:14]=2)=[CH:34][CH:35]=1)([CH3:28])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 81531DiisopropylethylamineHCID 8216924-(2-Pyridyl)Benzoic Acid

Product 1

HCID 11472986HCID 11472986, compound

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

The product from Example 1A (570 mg, 2.86 mmol) in SOCl2 (10 mL) was refluxed for 1 hour. The solution was allowed to cool to room temperature and SOCl2 was removed under reduced pressure. The residue was taken up in tetrahydrofuran (10 mL) and treated with DIEA (2.5 mL, 14.4 mmol, 5 eq) and 4tert-butylaniline (0.41 mL, 2.57 mmol). After stirring overnight at room temperature, the tetrahydrofuran was removed under reduced pressure and replaced with ethyl acetate (20 mL). The ethyl acetate was washed with H2O and brine, dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on silica gel (eluant gradient from 7:3 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate) to provide the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.26 (s, 1H), 8.71–8.74 (m, 1H), 8.23–8.26 (m, 2H), 8.07–8.10 (m, 3H), 7.94 (td, j=7.4 Hz, 2.1 Hz, 1H), 7.70–7.73 (m, 2H), 7.37–7.44 (m, 3H), 1.29 (s, 9H); MS (ESI+) m/z 331 (M+H)+.

Workup

  1. customSOCl2 was removed under reduced pressure
  2. customthe tetrahydrofuran was removed under reduced pressure
  3. washThe ethyl acetate was washed with H2O and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel (eluant gradient from 7:3 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-5275fd7fba04497cade926ee8cc5b5d6
Source dataset
uspto-grants-2006_05
Patent number
US07037927B2

Reaction notes

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