Triethylamine → HCID 178506375, compound

HRID 419741Notes

Reaction equation

HRID 419741 reaction equation
[F:1][C:2]([F:22])([F:21])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[NH:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1.Cl[C:24]1[N:32]=[CH:31][N:30]=[C:29]2[C:25]=1[NH:26][CH:27]=[N:28]2.C(N(CC)CC)C>CC(O)C>[F:22][C:2]([F:1])([F:21])[O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([CH:15]3[CH2:16][CH2:17][N:18]([C:24]4[N:32]=[CH:31][N:30]=[C:29]5[C:25]=4[NH:26][CH:27]=[N:28]5)[CH2:19][CH2:20]3)[NH:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53592776-ChloropurineHCID 178506376HCID 178506376, compound

Product 1

HCID 178506375HCID 178506375, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

Add 4-(4-(3-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)piperidine (200 mg, 0.642 mmol), 6-chloropurine (105 mg, 0.679 mmol), and triethylamine (95 μL, 0.681 mmol) to 2-propanol (5 mL). Heat the mixture at 80° C. for 3 h. Cool the mixture to room temperature and concentrate in vacuo. Triturate the solid in CH2Cl2 (10 mL). Purify the remaining solid by silica gel chromatography (60 g, eluting with 40% methanol/methylene chloride, 0.500 L) to provide 6-(4-(4-(3-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)piperidin-1-yl)-7H-purine (179 mg, 65%).

Workup

  1. temperatureCool the mixture to room temperature
  2. concentrationconcentrate in vacuo
  3. customTriturate the solid in CH2Cl2 (10 mL)
  4. customPurify the remaining solid
  5. washby silica gel chromatography (60 g, eluting with 40% methanol/methylene chloride, 0.500 L)

Sources & evidence

ORD record
ord-06ae26d13ac24e6ca8eeb1fb873fa3c6
Source dataset
uspto-grants-2012_01
Patent number
US08093383B2

Reaction notes

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