Ammonium Hydroxide → HCID 178490884, compound

HRID 1370138Notes

Reaction equation

HRID 1370138 reaction equation
[C:1]([C:4]1[CH:30]=[CH:29][C:7]2[N:8]([C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[C:9](=[O:21])[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([Cl:20])[CH:13]=3)[C:6]=2[CH:5]=1)([OH:3])=O.[OH-].[NH4+].Cl.C[N:35](C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>CN(C)C=O>[C:1]([C:4]1[CH:30]=[CH:29][C:7]2[N:8]([C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[C:9](=[O:21])[N:10]([CH2:11][C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([Cl:20])[CH:13]=3)[C:6]=2[CH:5]=1)(=[O:3])[NH2:35]

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178490885HCID 178490885, compound

Product 1

HCID 178490884HCID 178490884, compoundYield 303.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-carboxy-3-(3-chloro-4-methoxybenzyl)-1-(trans-4-hydroxycyclohexyl)-2,3-dihydro-1H-benzimidazol-2-one (72 mg), ammonium hydroxide (0.1 mL, 28% NH3 in water), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (35.2 mg) and 1-hydroxybenzotriazole (27.1 mg) in anhydrous dimethylformamide (1 mL) was stirred at ambient temperature for 4 hours. The mixture was partitioned between water and ethyl acetate. The separated organic layer was washed successively with an aqueous saturated sodium bicarbonate solution, water, 1N-hydrochloric acid and brine. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was subjected to a preparative silica gel column chromatography eluting with 5% methanol in chloroform. The obtained solid was washed with acetonitrile to give 5-carbamoyl-3-(3-chloro-4-methoxybenzyl)-1-(trans-4-hydroxycyclohexyl)-2,3-dihydro-1H-benzimidazol-2-one (217.9 mg) as a colorless solid.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe separated organic layer was washed successively with an aqueous saturated sodium bicarbonate solution, water, 1N-hydrochloric acid and brine
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated in vacuo
  5. washeluting with 5% methanol in chloroform
  6. washThe obtained solid was washed with acetonitrile

Sources & evidence

ORD record
ord-e37d2193b90b4363b8bf3118981663ea
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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