Tetrahydrofuran → HCID 54597163, compound

HRID 2174656Notes

Reaction equation

HRID 2174656 reaction equation
[CH:1]([S:4]([C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([C:20]#[C:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]([NH2:19])=[N:17][CH:18]=2)=[CH:9][CH:8]=1)(=[O:6])=[O:5])([CH3:3])[CH3:2].C1COCC1>CO.[Pd]>[CH:1]([S:4]([C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:16]([NH2:19])=[N:17][CH:18]=2)=[CH:11][CH:12]=1)(=[O:5])=[O:6])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 54670749HCID 54670749, compound

Product 1

HCID 54597163HCID 54597163, compoundYield 127.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd/C5% (20 mg, 0.1879 mmol) was added to a suspension of 5-(4-isopropylsulfonylphenyl)-3-(2-phenylethynyl)pyrazin-2-amine (100 mg, 0.1602 mmol) in MeOH (5 mL)/THF (5 mL) and the reaction stirred under an atmosphere of H2 for 1 hour. The catalyst was removed by filtration and the filtrate concentrated in vacuo. The material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were collected, and freeze-dried to give the di-TFA salt of the title compound as a yellow solid (78 mg, 80% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.17-1.20 (m, 6H), 2.99-3.03 (m, 2H), 3.10-3.14 (m, 2H), 3.43 (q, 1H), 7.19 (t, 1H), 7.33 (m, 4H), 7.87 (d, 2H), 8.22 (d, 2H) and 8.56 (s, 1H) ppm; (ES+) 382.0.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe material was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 μM, 100 Å column, gradient 10%-95% B (solvent A: 0.05% TFA in water; solvent B: CH3CN) over 16 minutes at 25 mL/min]
  4. customThe fractions were collected
  5. customfreeze-dried

Sources & evidence

ORD record
ord-a5664ed72c5a4aca96569e48b50a71b0
Source dataset
uspto-grants-2015_06
Patent number
US09062008B2

Reaction notes

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