4-Phenylbenzylamine → HCID 68109765, compound

HRID 2363678Notes

Reaction equation

HRID 2363678 reaction equation
[CH:1]([C:4]1[CH:5]=[N:6][N:7]2[C:12]([N:13]([CH3:20])C3C=CC=CC=3)=[N:11][C:10]([S:21][CH3:22])=[N:9][C:8]=12)([CH3:3])[CH3:2].[C:23]1([C:29]2[CH:36]=[CH:35][C:32](CN)=[CH:31][CH:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CO>[CH:1]([C:4]1[CH:5]=[N:6][N:7]2[C:12]([NH:13][CH2:20][C:32]3[CH:35]=[CH:36][C:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[CH:30][CH:31]=3)=[N:11][C:10]([S:21][CH3:22])=[N:9][C:8]=12)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 3449894-PhenylbenzylamineHCID 25210248HCID 25210248, compound

Product 1

HCID 68109765HCID 68109765, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a sealed tube, a solution of 8-isopropyl-4-(N-methyl-N-phenylamino)-2-(methylsulfanyl)pyrazolo[1,5-a]-1,3,5-triazine (114 mg, 0.36 mmol) and of 4-phenylbenzylamine (100 mg, 0.55 mmol) is heated at 140° C. for 24 h. After cooling, the solvent is evaporated off. The crude compound collected is purified by flash chromatography (EP/Et2O 9:1) so as to give IIa.1 (95 mg, 67%). Mp=134-135° C. (MeOH). 1H NMR (300 MHz, CDCl3): δ 7.75 (s, 1H, Harom), 7.59-7.56 (m, 4H, Harom), 7.45-7.34 (m, 5H, Harom), 6.93 (bs, 1H, NH), 4.85 (d, 2H, J=5.7 Hz, CH2), 3.18 (hept, 1H, J=7.2 Hz, CH), 2.58, (s, 3H, CH3), 1.33 (d, 6H, J=7.2 Hz, 2 CH3). MS (EST): m/z 390 (MH′).

Workup

  1. temperatureAfter cooling
  2. customthe solvent is evaporated off
  3. customThe crude compound collected
  4. customis purified by flash chromatography (EP/Et2O 9:1) so as
  5. customto give IIa.1 (95 mg, 67%)

Sources & evidence

ORD record
ord-705da97e034244c081e32f2485e8b840
Source dataset
uspto-grants-2014_04
Patent number
US08691982B2

Reaction notes

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