Triethylamine → HCID 59223043, compound

HRID 2386919Notes

Reaction equation

HRID 2386919 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[N:5]=[C:4]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][CH2:20][NH:21][C:22]3[C:31]4[C:26](=[C:27]([F:33])[CH:28]=[CH:29][C:30]=4[F:32])[N:25]=[CH:24][N:23]=3)=[CH:15][CH:14]=2)[CH:3]=1.C(N(CC)CC)C.[H][H]>CCO.[Pd]>[F:32][C:30]1[CH:29]=[CH:28][C:27]([F:33])=[C:26]2[C:31]=1[C:22]([NH:21][CH2:20][CH2:19][C:16]1[CH:15]=[CH:14][C:13]([O:12][C:4]3[CH:3]=[CH:2][N:7]=[C:6]([C:8]([F:9])([F:10])[F:11])[N:5]=3)=[CH:18][CH:17]=1)=[N:23][CH:24]=[N:25]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 59222956HCID 59222956, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59223043HCID 59223043, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of {2-[4-(6-chloro-2-trifluoromethylpyrimidin-4-yloxy)-phenyl]-ethyl}-(5,8-difluoroquinazolin-4-yl)-amine (0.205 g, 0.46 mmol), 10% Pd on activated carbon (0.030 g) and triethylamine (0.60 mL, 4.3 mmol) in EtOH (15 mL) was charged with hydrogen to an initial pressure of 40 psi in a Parr bottle and shaken overnight. The catalyst was removed by filtration on Celite and the filtrate was concentrated in vacuo. The residue was purified on silica gel to give 0.087 g (42% yield) of (5,8-difluoroquinazolin-4-yl)-{2-[4-(2-trifluoromethylpyrimidin-4-yloxy)-phenyl]-ethyl}-amine as a white foam, 1H NMR (CDCl3): δ 8.71 (d, J=6.3 Hz, 1H), 8.69 (s, 1H), 7.32-7.40 (m, 3H), 7.16 (d, J=8.7 Hz, 2H), 6.97-7.04 (m, 2H), 6.68-6.82 (br, 1H), 3.97 (q, J=6.9 Hz, 2H), 3.08 (t, J=6.9 Hz, 2H). LC/MS: 448.18 (M++1).

Workup

  1. customThe catalyst was removed by filtration on Celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified on silica gel

Sources & evidence

ORD record
ord-d65c953913484fca951168b3df3b4311
Source dataset
uspto-grants-2012_09
Patent number
US08268843B2

Reaction notes

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