Hydrochloric Acid → HCID 10310783, compound

HRID 2416921Notes

Reaction equation

HRID 2416921 reaction equation
[CH:1]1([N:7]([CH3:33])[C:8]([C:10]2[CH:32]=[CH:31][C:13]3[N:14]([CH2:25][CH2:26][CH2:27][C:28](O)=[O:29])[C:15]([NH:17][C:18]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[O:19])=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O[N:36]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[OH-].[NH4+].Cl>CN(C=O)C>[CH:1]1([N:7]([CH3:33])[C:8]([C:10]2[CH:32]=[CH:31][C:13]3[N:14]([CH2:25][CH2:26][CH2:27][C:28](=[O:29])[NH2:36])[C:15]([NH:17][C:18]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[O:19])=[N:16][C:12]=3[CH:11]=2)=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 10195437HCID 10195437, compound

Product 1

HCID 10310783HCID 10310783, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{5-(N-cyclohexyl-N-methyl-carbamoyl)-2-[(thiophene-2-carbonyl)-amino]-benzoimidazol-1-yl}-butyric acid (Example 2) (0.05 g, 11 mmol) in DMF (5 mL) was added 1-hydroxybenzotriazole hydrate (0.02 g, 16 mmol) followed by 1-[3-(dimethylamino)propyl]-3-ethylcarbodimide hydrochloride (0.03 g, 16 mmol). The mixture was stirred for 1 h., and ammonium hydroxide (5 mL) was added. Stirring was continued for 48 h. The solution was neutralized with 1M HCl, and partitioned between EtOAc (10 mL) and water (10 mL). The organic layer was washed with saturated sodium carbonate (10 mL) and water (3×10 mL). The solvent was evaporated and the resulting oil was purified by flash chromatography with 5% MeOH/dichloromethane to give the title compound (0.02 g, 40%), m.p. 112-115° C.

Workup

  1. stirringStirring
  2. waitwas continued for 48 h
  3. custompartitioned between EtOAc (10 mL) and water (10 mL)
  4. washThe organic layer was washed with saturated sodium carbonate (10 mL) and water (3×10 mL)
  5. customThe solvent was evaporated
  6. customthe resulting oil was purified by flash chromatography with 5% MeOH/dichloromethane

Sources & evidence

ORD record
ord-de9a3608a8c14cef974404d790ee6854
Source dataset
uspto-grants-2004_11
Patent number
US06825219B2

Reaction notes

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