Hydrochloric Acid → HCID 178482251, compound

HRID 1092144Notes

Reaction equation

HRID 1092144 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([NH:19][C:20]([C:22]3[N:23]=[CH:24][C:25]([N:28]4[CH2:32][CH2:31][CH:30]([N:33](C)[C:34](=O)OC(C)(C)C)[CH2:29]4)=[N:26][CH:27]=3)=[O:21])[NH:17][N:18]=2)[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1>CO>[CH3:2][O:3][C:4]1[CH:5]=[C:6]([CH2:12][CH2:13][C:14]2[CH:15]=[C:16]([NH:19][C:20]([C:22]3[CH:27]=[N:26][C:25]([N:28]4[CH2:32][CH2:31][CH:30]([NH:33][CH3:34])[CH2:29]4)=[CH:24][N:23]=3)=[O:21])[NH:17][N:18]=2)[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 178489794HCID 178489794, compound

Product 1

HCID 178482251HCID 178482251, compoundYield 39.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Hydrogen chloride (4M in dioxane, 0.57 mL, 2.26 mmol) was added to tert-butyl N-[1-[5-[[5-[2-(3,5-dimethoxyphenyl)ethyl]-2H-pyrazol-3-yl]carbamoyl]pyrazin-2-yl]pyrrolidin-3-yl]-N-methylcarbamate (312 mg, 0.57 mmol) in methanol (2.80 mL) at 25° C. The resulting solution was stirred at room temperature for 48 h. The reaction was incomplete and further hydrogen chloride (4M in dioxane, 0.28 mL, 1.12 mmol) was added and the solution was stirred at room temperature for a further 16 h. The reaction mixture was diluted with MeOH (5 ml) and the crude product was purified by ion exchange chromatography, using a SCX column. The desired product was eluted from the column using 7M NH3/MeOH and fractions were evaporated to dryness to afford impure product. The crude product was purified by preparative HPLC, using decreasingly polar mixtures of water (containing 1% NH3) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford the title compound (101 mg, 39%) as a white solid.

Workup

  1. stirringthe solution was stirred at room temperature for a further 16 h
  2. customthe crude product was purified by ion exchange chromatography
  3. washThe desired product was eluted from the column
  4. customwere evaporated to dryness
  5. customto afford impure product
  6. customThe crude product was purified by preparative HPLC
  7. additionFractions containing the desired compound
  8. customwere evaporated to dryness

Sources & evidence

ORD record
ord-675068188cec40a6a4299faf76c6d65d
Source dataset
uspto-grants-2012_03
Patent number
US08129391B2

Reaction notes

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