4-Tert-Butylaniline → HCID 2111998, compound

HRID 736372Notes

Reaction equation

HRID 736372 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][CH:4]=1)#[N:2].CCN(C(C)C)C(C)C.[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22]>O1CCCC1>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:7](=[O:8])[C:6]2[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)=[CH:30][CH:31]=1)([CH3:24])([CH3:22])[CH3:23]

Participants

5

Reactant 3

HCID 698614-Tert-ButylanilineHCID 801724-Cyanobenzoyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 2111998HCID 2111998, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-cyanobenzoyl chloride (2 g, 12.08 mmol), DIEA (7.3 mL, 42 mmol), and 4-tert-butylaniline (1.9 mL, 11.9 mmol) were stirred in tetrahydrofuran (50 mL) overnight at room temperature. The tetrahydrofuran was removed under reduced pressure and replaced with ethyl acetate. The ethyl acetate was washed with H2O and brine, dried over Na2SO4, filtered, and the filtrate concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluant gradient from 8:2 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate) to afford the title compound as a solid. 1H NMR (300 MHz, DMSO-d6) δ 10.41 (s, 1H), 8.08-8.12 (m, 2H), 8.01-8.04 (m, 2H), 7.66-7.69 (m, 2H), 7.37-7.41 (m, 2H), 1.28 (s, 9H); MS (ESI+) m/z 279 (M+H)+.

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. washThe ethyl acetate was washed with H2O and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluant gradient from 8:2 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-32e45f698db047d4b8425cb819d8b26a
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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