4-Tert-Butylaniline → HCID 11472986, compound

HRID 736370Notes

Reaction equation

HRID 736370 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 4-tert-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-974ce9f67c884a03bc8262baa9cc1ce8
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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