Hydrochloric Acid → HCID 72549749, compound

HRID 626919Notes

Reaction equation

HRID 626919 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([F:17])([F:16])[F:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([C@@H:18]2[CH2:22][CH2:21][C@@:20]3([CH2:26][CH2:25][NH:24][C:23]3=[O:27])[N:19]2C(OC(C)(C)C)=O)[N:3]=1.Cl.O1CCOCC1>C(Cl)Cl>[NH3:3].[CH3:23][OH:27].[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([F:15])([F:16])[F:17])=[CH:12][CH:13]=2)[N:5]=[C:4]([C@@H:18]2[CH2:22][CH2:21][C@@:20]3([CH2:26][CH2:25][NH:24][C:23]3=[O:27])[NH:19]2)[N:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 131735231HCID 131735231, compound

Product 2

HCID 21705897Ammonia methanolHCID 72549749HCID 72549749, compoundYield 205.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl (2S,5S)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-6-oxo-1,7-diazaspiro[4.4]nonane-1-carboxylate (37 mg, 0.0800 mmol) was added to a stirred solution of 4M HCl in 1,4-dioxan (2 mL, 8 mmol) in DCM (2 mL) at ambient temperature. The colourless solution was stirred in a stoppered flask for 4 h. The solution was evaporated and re-evaporated with toluene (25 ml). The residue was dissolved in MeOH (2 ml) and passed through a 2 g SCX cartridge, eluting with MeOH then 1M NH3-MeOH to give (2S,5S)-2-[4-methyl-6-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one (31 mg);

Workup

  1. customThe solution was evaporated
  2. customre-evaporated with toluene (25 ml)
  3. dissolutionThe residue was dissolved in MeOH (2 ml)
  4. washeluting with MeOH

Sources & evidence

ORD record
ord-bbfbdaaba54a49e997917ec7afbda1a0
Source dataset
uspto-grants-2016_04
Patent number
US09309254B2

Reaction notes

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