HCID 69811015, compound → HCID 178462032, compound

HRID 535754Notes

Reaction equation

HRID 535754 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([C:33]2([CH3:36])[CH2:35][CH2:34]2)[N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C@@H:15]([NH:17]C(=O)OC(C)(C)C)[CH3:16])[N:8]=1>Cl.CO>[Br:1][C:2]1[N:3]=[C:4]([C:33]2([CH3:36])[CH2:35][CH2:34]2)[NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH2:14][C@@H:15]([NH2:17])[CH3:16])[N:8]=1

Participants

4

Reactant 1

HCID 69811015HCID 69811015, compound

Product 1

HCID 178462032HCID 178462032, compoundYield 136%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of (S)-tert-butyl 1-(4-(4-bromo-2-(1-methylcyclopropyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate (2.46 g, 4.23 mmol) in concentrated HCl (1.3 mL) and MeOH (20 mL) was stirred at room temperature overnight. LCMS indicated only 30% conversion; the reaction was then heated at 60° C. for 4 hours and stirred overnight at room temperature. LCMS indicated complete conversion and the reaction mixture was concentrated to a yellow solid to afford the crude (S)—N1-(4-(4-bromo-2-(1-methylcyclopropyl)-1H-imidazol-5-yl)pyrimidin-2-yl)propane-1,2-diamine (2.02 g) as the HCl salt which is used in next step without purification: LCMS (m/z) 351.1 (MH+), tR=0.45 minute.

Workup

  1. temperaturethe reaction was then heated at 60° C. for 4 hours
  2. stirringstirred overnight at room temperature
  3. concentrationthe reaction mixture was concentrated to a yellow solid

Sources & evidence

ORD record
ord-586a101696584de49d98680ecf35a3d4
Source dataset
uspto-grants-2014_10
Patent number
US08859548B2

Reaction notes

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