HCID 69810901, compound → HCID 178462030, compound

HRID 535765Notes

Reaction equation

[Br:1][C:2]1[N:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][CH:34]=2)[N:5](COCC[Si](C)(C)C)[C:6]=1[C:7]1[N:12]=[C:11]([NH:13][CH2:14][C@@H:15]([NH:17]C(=O)OC(C)(C)C)[CH3:16])[CH:10]=[CH:9][N:8]=1>Cl.CO>[Br:1][C:2]1[N:3]=[C:4]([C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:35][CH:34]=2)[NH:5][C:6]=1[C:7]1[N:12]=[C:11]([NH:13][CH2:14][C@@H:15]([NH2:17])[CH3:16])[CH:10]=[CH:9][N:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

The mixture of (S)-tert-butyl 1-(2-(4-bromo-2-(4-(trifluoromethyl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-5-yl)pyrimidin-4-ylamino)propan-2-ylcarbamate (0.14 g, 0.21 mmol) in concentrated HCl (0.24 mL) and MeOH (5 mL) was heated at 80° C. for 3 hours, then stirred at room temperature overnight. The reaction mixture was concentrated to a yellow solid to afford crude (S)—N1-(2-(4-bromo-2-(4-(trifluoromethyl)phenyl)-1H-imidazol-5-yl)pyrimidin-4-yl)propane-1,2-diamine (0.12 g) as the HCl salt, which is used in next step without purification: LCMS (m/z) 441.0 (MH+), tR=0.68 minute.

Workup

concentrationThe reaction mixture was concentrated to a yellow solid

Sources & evidence

ORD record: ord-d366863a27b5471c90c9f09d1ba017e9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859548B2

Reaction notes

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