Hydrochloric Acid → HCID 118061573, compound

HRID 575532Notes

Reaction equation

HRID 575532 reaction equation
[NH2:1][C:2]1[C:7]([CH2:8][CH2:9][CH:10]2[CH2:15][CH2:14][N:13]([C:16](=[O:27])[C@@H:17]([NH:19]C(=O)OC(C)(C)C)[CH3:18])[CH2:12][CH2:11]2)=[C:6]([Cl:28])[N:5]=[C:4]([CH3:29])[N:3]=1.O1CCOCC1.Cl>CO>[ClH:28].[NH2:19][C@@H:17]([CH3:18])[C:16]([N:13]1[CH2:14][CH2:15][CH:10]([CH2:9][CH2:8][C:7]2[C:2]([NH2:1])=[N:3][C:4]([CH3:29])=[N:5][C:6]=2[Cl:28])[CH2:11][CH2:12]1)=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 118061845HCID 118061845, compound

Product 1

HCID 118061573HCID 118061573, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add tert-butyl N-[(1S)-2-[4-[2-(4-amino-6-chloro-2-methyl-pyrimidin-5-yl)ethyl]-1-piperidyl]-1-methyl-2-oxo-ethyl]carbamate (28.75 g, 67.49 mmol) to 1,4-dioxane (143.7 mL). Then add 4M hydrogen chloride in 1,4-dioxane (168.7 mL, 674.9 mmol) and stir for 10 min. Add MeOH (20 mL) and stir the mixture for 3 h with vigorous stirring. Concentrate the mixture under reduced pressure, dilute the solids with diethyl ether (200 mL), and stir overnight. Filter the material, rinsing with diethyl ether (2×25 mL). Dry the material via suction for 15 min, then place under vacuum for 1 h at 45° C. to obtain the title compound as a crude white powder (27.7 g). LC-ES/MS m/z (35Cl/37Cl) 326.1/328.2 (M+1).

Workup

  1. concentrationConcentrate the mixture under reduced pressure
  2. additiondilute the solids with diethyl ether (200 mL)
  3. stirringstir overnight
  4. filtrationFilter the material
  5. washrinsing with diethyl ether (2×25 mL)
  6. customDry the material via suction for 15 min

Sources & evidence

ORD record
ord-605dc3c6e8294a28aa3ed87da6129bc6
Source dataset
uspto-grants-2015_05
Patent number
US09035051B1

Reaction notes

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