Hydrochloric Acid → HCID 67975407, compound

HRID 537847Notes

Reaction equation

HRID 537847 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]([CH2:28][CH2:29][CH2:30][CH2:31][F:32])[C:7]([CH2:9][N:10]3[C:14]4[CH:15]=[N:16][CH:17]=[CH:18][C:13]=4[N:12]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[C:11]3=[O:27])=[N:8][C:4]=2[CH:3]=1.[OH-].[Li+].Cl.ClCCl>O1CCCC1.O.O>[Cl:1][C:2]1[CH:34]=[CH:33][C:5]2[N:6]([CH2:28][CH2:29][CH2:30][CH2:31][F:32])[C:7]([CH2:9][N:10]3[C:14]4[CH:15]=[N:16][CH:17]=[CH:18][C:13]=4[N:12]([CH2:19][C:20]([OH:22])=[O:21])[C:11]3=[O:27])=[N:8][C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 6344DichloromethaneHCID 67992693HCID 67992693, compound

Product 1

HCID 67975407HCID 67975407, compoundYield 106.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

In a 100 mL dry flask, tert-butyl (3-{[5-chloro-1-(4-fluorobutyl)-1H-benzimidazol-2-yl]methyl}-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)acetate (P33) (1.74 g, 3.49 mmol) was dissolved in 50 mL tetrahydrofuran/water mixture (3/1). Lithium hydroxide (167.3 mg, 6.98 mmol, 2 eq.) was added to the solution and the mixture was stirred for 16 hours at room temperature. The reaction mixture was diluted with water (20 mL) followed by the addition of aqueous HCl (1M) until the pH was approximately 6. Dichloromethane (40 mL) was added to the reaction mixture and the organic layer separated. The aqueous layer was evaporated to dryness and dried into the oven during 16 hours to give (3-{[5-chloro-1-(4-fluorobutyl)-1H-benzimidazol-2-yl]methyl}-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]pyridin-1-yl)acetic acid (P67, 1.6 g, 100%) as a white solid; LCMS m/z=432 (M+H)+

Workup

  1. customIn a 100 mL dry flask
  2. customthe organic layer separated
  3. customThe aqueous layer was evaporated to dryness
  4. customdried into the oven during 16 hours

Sources & evidence

ORD record
ord-857b106bfefd4883bd4b006784328d66
Source dataset
uspto-grants-2014_10
Patent number
US08865705B2

Reaction notes

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