Hydrochloric Acid → HCID 136138783, compound

HRID 2365430Notes

Reaction equation

HRID 2365430 reaction equation
[CH2:1]([N:8]([CH2:30][CH2:31][O:32][Si](C(C)(C)C)(C)C)[C:9]1[N:14]=[C:13]2[NH:15][CH:16]=[C:17]([C:18]3[NH:22][N:21]=[CH:20][C:19]=3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[C:12]2=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:40].O1CCOCC1>CO>[ClH:29].[ClH:40].[CH2:1]([N:8]([C:9]1[N:14]=[C:13]2[NH:15][CH:16]=[C:17]([C:18]3[NH:22][N:21]=[CH:20][C:19]=3[C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=3)[C:12]2=[CH:11][CH:10]=1)[CH2:30][CH2:31][OH:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 312751,4-DioxaneHCID 136338082HCID 136338082, compound

Product 1

HCID 136138783HCID 136138783, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of crude N-benzyl-N-(2-((tert-butyldimethylsilyl)oxy)ethyl)-3-(4-(3-chlorophenyl)-1H-pyrazol-5-yl)-1H-pyrrolo[2,3-b]pyridin-6-amine (78 mg, 0.14 mmol) in methanol (5 mL) was added a 4M solution of hydrogen chloride in dioxane (5 mL, 20 mmol) and the solution stirred at room temperature for 2 hours. After this time the reaction was concentrated and the residue purified by preparative HPLC. Concentration of the product containing fractions afforded a solid that was re-dissolved in MeOH (5 mL) and treated with 2N HCl (2 mL). The solution was then re-concentrated, the residue co-evaporated with acetonitrile (5 mL) then dissolved in water (5 mL). Subsequent isolation by lyophilization afforded the title compound as a yellow solid in 25% yield over 2 steps.

Workup

  1. concentrationAfter this time the reaction was concentrated
  2. customthe residue purified by preparative HPLC
  3. additionConcentration of the product containing fractions
  4. customafforded a solid
  5. concentrationThe solution was then re-concentrated
  6. dissolutionthe residue co-evaporated with acetonitrile (5 mL) then dissolved in water (5 mL)

Sources & evidence

ORD record
ord-b449ae16c96548d3ac88c927d3abde74
Source dataset
uspto-grants-2014_04
Patent number
US08697697B2

Reaction notes

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