HCID 69812887, compound → HCID 178462033, compound

HRID 535760Notes

Reaction equation

HRID 535760 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH:33]2[CH2:36][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]([CH:33]2[CH2:36][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 69812887HCID 69812887, compound

Product 1

HCID 178462033HCID 178462033, compoundYield 151.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ((S)-tert-butyl 1-(4-(4-bromo-2-cyclobutyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-2-ylamino)propan-2-ylcarbamate (0.27 g, 0.47 mmol) in concentrated HCl (0.14 mL) and MeOH (4 mL) was heated to 80° C. for 5 hours. The reaction mixture was allowed to cool to room temperature and concentrated to a yellow solid to afford the crude (S)—N1-(4-(4-bromo-2-cyclobutyl-1H-imidazol-5-yl)pyrimidin-2-yl)propane-1,2-diamine (0.25 g) as the HCl salt which is used in next step without purification: LCMS (m/z) 351.0 (MH+), tR=0.45 minute.

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-7b1bbec1a5e1473eb8081986c39e8ed3
Source dataset
uspto-grants-2014_10
Patent number
US08859548B2

Reaction notes

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