Hydrochloric Acid → HCID 66656409, compound

HRID 517780Notes

Reaction equation

HRID 517780 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][N:15]3[CH2:20][C@@H:19]4[CH2:21][C@H:16]3[CH2:17][N:18]4C(OC(C)(C)C)=O)=[N:12][N:11]=[N:10]2)=[CH:5][CH:4]=1.Cl.O1CCOCC1>CO>[F:30][C:2]([F:1])([F:29])[C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([CH2:14][N:15]3[CH2:20][C@@H:19]4[CH2:21][C@H:16]3[CH2:17][NH:18]4)=[N:12][N:11]=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 68297709HCID 68297709, compound2×

Product 1

HCID 66656409HCID 66656409, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (1S,4S)-5-({1-[4-(trifluoromethyl)phenyl]-1H-tetrazol-5-yl}methyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (470 mg, 1.107 mmol, Intermediate 17) in methanol was added 4M hydrogen chloride in 1,4-dioxane (5 mL, 20 mmol). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and poured onto a 5 g SCX cartridge. The cartridge was washed with methanol (2 column volumes) and eluted with ammonia in methanol (2 column volumes). The ammonia in methanol fractions were concentrated and the residue dried in vacuo to yield the title compound as white crystals (363 mg)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionpoured onto a 5 g SCX cartridge
  3. washThe cartridge was washed with methanol (2 column volumes)
  4. washeluted with ammonia in methanol (2 column volumes)
  5. concentrationThe ammonia in methanol fractions were concentrated
  6. customthe residue dried in vacuo

Sources & evidence

ORD record
ord-28bc916c733b40638d6d199f28b8680d
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

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