Triethylamine → HCID 59222942, compound

HRID 1467414Notes

Reaction equation

HRID 1467414 reaction equation
[Cl:1][C:2]1[C:3]([C:31]([F:34])([F:33])[F:32])=[N:4][CH:5]=[C:6](Cl)[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][NH:17][C:18]2[C:27]3[C:22](=[C:23]([F:29])[CH:24]=[CH:25][C:26]=3[F:28])[N:21]=[CH:20][N:19]=2)=[CH:11][CH:10]=1.C(N(CC)CC)C>CCO.[Pd]>[Cl:1][C:2]1[C:3]([C:31]([F:33])([F:34])[F:32])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][NH:17][C:18]2[C:27]3[C:22](=[C:23]([F:29])[CH:24]=[CH:25][C:26]=3[F:28])[N:21]=[CH:20][N:19]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 59222940HCID 59222940, compound

Product 1

HCID 59222942HCID 59222942, compoundYield 0%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

{2-[4-(3,5-dichloro-2-trifluoromethylpyridin-4-yloxy)-phenyl]-ethyl}-(5,8-difluoroquinazolin-4-yl)-amine (700 mg, 1.4 mol) was dissolved in 2B EtOH (100 mL) under nitrogen in a Parr shaker bottle. Triethylamine (130 mg) and 10% Pd/C (200 mg) were added and the bottle was charged with H2 to an initial pressure of 50 psi. After shaking for approx. 10 min (approx 1 psi H2 uptake), the reaction was filtered through Celite and concentrated in vacuo to provide a white solid. The solid was partitioned between water and EtOAc twice, and the pooled fractions were dried and concentrated in vacuo. The residue was triturated with Et2O, to afford 310 mg of {2-[4-(3-chloro-2-trifluoromethylpyridin-4-yloxy)-phenyl]-ethyl}-(5,8-difluoroquinazolin-4-yl)-amine as a white crystalline solid, M.P. 129-131°. 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.35 (d, J=5.4 Hz, 1H), 7.40-7.31 (m, 3H), 7.12-7.06 (m, 2H), 7.05-6.97 (m, 1H), 6.85-6.66 (m, 2H), 4.01-3.92 (m, 2H), 3.09 (t, J=7.1 Hz, 2H); MS: m/z 480.

Workup

  1. additionthe bottle was charged with H2 to an initial pressure of 50 psi
  2. filtrationthe reaction was filtered through Celite
  3. concentrationconcentrated in vacuo
  4. customto provide a white solid
  5. customThe solid was partitioned between water and EtOAc twice
  6. customthe pooled fractions were dried
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-059dd44bbf31442295579c62f53c75e9
Source dataset
uspto-grants-2015_04
Patent number
US09000162B2

Reaction notes

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