Triethylamine → HCID 11165107, compound

HRID 736390Notes

Reaction equation

HRID 736390 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[N:7]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[N:6]=[CH:5][CH:4]=1.[C:19]([C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C>CN(C=O)C>[C:19]([C:23]1[CH:24]=[CH:25][C:26]([NH:27][C:12](=[O:14])[C:11]2[CH:10]=[CH:9][C:8]([N:7]3[C:3]([C:2]([F:1])([F:18])[F:17])=[CH:4][CH:5]=[N:6]3)=[CH:16][CH:15]=2)=[CH:28][CH:29]=1)([CH3:22])([CH3:20])[CH3:21]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 698614-Tert-ButylanilineHCID 757711-HydroxybenzotriazoleHCID 22170448HCID 22170448, compound

Product 1

HCID 11165107HCID 11165107, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

The product from Example 37A (37.3 mg, 0.146 mmol), 4-tert-butylaniline (28 μL, 0.18 mmol), PS-DCC (1.27 mmol/g, 0.342 g, 0.435 mmol), HOBT (20.2 mg, 0.149 mmol), and triethylamine (0.062 mL, 0.45 mmol) in DMF (1.5 mL) were combined and heated at 65° C. for 16 hours. The mixture was allowed to cool to room temperature, filtered, and the filtrate was diluted with diethyl ether (20 mL). The diethyl ether was washed with water (10 mL), brine (10 mL), dried (Na2SO4), filtered, and the filtrate concentrated under reduced pressure. The residue was purified by flash chromatography (15% ethyl acetate in hexanes) to provide the title compound as a solid. 1H NMR (300 MHz, CDCl3) δ 7.99 (d, 2H), 7.83 (br s, 1H), 7.76 (m, 1H), 7.63 (d, 2H), 7.52 (d, 2H), 7.41 (d, 2H), 6.87 (m, 1H), 1.33 (s, 9H); MS (m/z) 388.

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered
  3. additionthe filtrate was diluted with diethyl ether (20 mL)
  4. washThe diethyl ether was washed with water (10 mL), brine (10 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under reduced pressure
  8. customThe residue was purified by flash chromatography (15% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-14aa091eb7de4ae790605fc249ec6c7f
Source dataset
uspto-grants-2009_09
Patent number
US07595332B2

Reaction notes

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