Hydrochloric Acid → HCID 178477890, compound

HRID 1842485Notes

Reaction equation

HRID 1842485 reaction equation
Cl.[Cl:2][C:3]1[CH:22]=[CH:21][C:6]2[NH:7][C:8]([CH:10]3[CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11]3)=[N:9][C:5]=2[CH:4]=1.CO>O1CCOCC1>[NH:12]1[CH2:13][CH:10]([C:8]2[NH:7][C:6]3[CH:21]=[CH:22][C:3]([Cl:2])=[CH:4][C:5]=3[N:9]=2)[CH2:11]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178451646HCID 178451646, compound

Product 1

HCID 178477890HCID 178477890, compoundYield 62.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Hydrochloric acid, 4.0 m solution in 1,4-dioxane (16.25 mL, 65.0 mmol) was added to a solution of tert-butyl 3-(5-chloro-1H-benzo[d]imidazol-2-yl)azetidine-1-carboxylate (2 g, 6.50 mmol) in dioxane (20 ml) under argon. MeOH (20 mL) was added to the resulting suspension to make a solution and the mixture was stirred for 2 h at RT, at which time it turned back to a suspension. The mixture was filtered and the collected solid was washed with dioxane and air dried to give product as a white solid (840 mg). The filtrate was then concentrated and then dissolved in a minimum of MeOH. Et2O was added slowly and the resulting suspension was filtered and dried to give an additional 560 mg product as a light grey solid.

Workup

  1. filtrationThe mixture was filtered
  2. washthe collected solid was washed with dioxane and air
  3. customdried

Sources & evidence

ORD record
ord-08bef4eb658445998ac94cf29f8bcaab
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

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