Water → HCID 135837633, compound

HRID 1835086Notes

Reaction equation

HRID 1835086 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH2:11][CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][N:17]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=2)[CH2:16][CH2:15]1.[OH2:30]>>[F:27][C:26]([F:29])([F:28])[C:22]1[CH:21]=[C:20]([N:17]2[CH2:18][CH2:19][N:14]([CH2:13][CH2:12][CH2:11][N:6]3[CH:5]=[N:4][C:3]4[C:2](=[O:30])[NH:10][CH:9]=[N:8][C:7]3=4)[CH2:15][CH2:16]2)[CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 2

HCID 962WaterHCID 23502880HCID 23502880, compound

Product 1

HCID 135837633HCID 135837633, compound

Procedure

6-Chloro-9-{3-[4-(3-trifluoromethylphenyl)piperazin-1-yl]propyl}-9H-purine (200 mg) was dissolved in 3 mL of trifluoroacetic acid(TFA) and 1 mL of water and stirred for 16 hours at 25 C. The TFA was evaporated and 10 mL of 2N NaOH was added. The solution was extracted twice with 20 mL of dichloromethane. The organic layer was separated, dried with sodium sulfate and concentrated to give the title compound as an oil. The oil was dissolved in 5 mL of 50% dichloromethane in hexanes. A solution of 4N HCl in dioxane (200 uL) was added and the mixture stirred for 30 minutes followed by vacuum filtration of the suspension. A white powder of the product HCl salt was recovered.

Workup

  1. customThe TFA was evaporated
  2. addition10 mL of 2N NaOH was added
  3. extractionThe solution was extracted twice with 20 mL of dichloromethane
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-713ca842b14743299d9583fa17b6ab0d
Source dataset
uspto-grants-2004_08
Patent number
US06770638B2

Reaction notes

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