Hydrochloric Acid → HCID 136337441, compound

HRID 1481530Notes

Reaction equation

HRID 1481530 reaction equation
[C:1]([C:5]1[C:6]([Cl:31])=[C:7]([C:11]2[NH:19][C:18]3[C:13](=[N:14][C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:30])([F:29])[F:28])=[N:16][C:17]=3[CH3:20])[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl>CCO>[ClH:31].[C:1]([C:5]1[C:6]([Cl:31])=[C:7]([C:11]2[NH:19][C:18]3[C:13](=[N:14][C:15]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[C:27]([F:29])([F:28])[F:30])=[N:16][C:17]=3[CH3:20])[N:12]=2)[N:8]([CH3:10])[N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 136073174HCID 136073174, compound

Product 1

HCID 136337441HCID 136337441, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 8-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-methyl-2-(2-trifluoromethyl-phenyl)-7H-purine (99.7 mg, 0.222 mmol, prepared as in STEP B above) in EtOH (6 mL) was treated with HCl (44.4 μL, 0.222 mmol, 5 M in IPA) at room temperature for 1.5 h and concentrated in vacuo. EtOH (0.5 mL) was added, and the resulting glassy solid was dissolved using sonication and heating. Hexanes (5 mL) were added, and the resulting mixture was concentrated in vacuo. The resulting foamy solid was triturated with hexanes, filtered, and air-dried to yield 8-(5-tert-butyl-4-chloro-2-methyl-2H-pyrazol-3-yl)-6-methyl-2-(2-trifluoromethyl-phenyl)-7H-purine hydrochloride as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 7.82-8.03 (m, 2H), 7.65-7.82 (m, 2H), 4.39 (s, 3H), 3.34 (br. s., 3H), 1.45 (s, 9H). Mass Spectrum (LCMS, APCI pos.): Calculated for C21H20N6ClF3: 449.1 (M+H). Measured: 449.2.

Workup

  1. concentrationconcentrated in vacuo
  2. additionEtOH (0.5 mL) was added
  3. dissolutionthe resulting glassy solid was dissolved
  4. customsonication
  5. temperatureheating
  6. additionHexanes (5 mL) were added
  7. concentrationthe resulting mixture was concentrated in vacuo
  8. customThe resulting foamy solid was triturated with hexanes
  9. filtrationfiltered
  10. customair-dried

Sources & evidence

ORD record
ord-2e38664970d84df1883a6c232e684517
Source dataset
uspto-grants-2016_08
Patent number
US09409915B2

Reaction notes

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