Hydrochloric Acid → HCID 21088561, compound

HRID 350753Notes

Reaction equation

HRID 350753 reaction equation
Cl.[F:2][C:3]([P:12](=[O:19])([O:16][CH2:17][CH3:18])[O:13][CH2:14][CH3:15])([F:11])[C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1.[N:20]1([C:29]2[O:30][C:31]([CH2:41][CH2:42][C:43](O)=[O:44])=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[N:33]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[CH:21]1.ON1C2N=CC=CC=2N=N1.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[N:20]1([C:29]2[O:30][C:31]([CH2:41][CH2:42][C:43]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([C:3]([P:12]([O:16][CH2:17][CH3:18])([O:13][CH2:14][CH3:15])=[O:19])([F:2])[F:11])=[CH:5][CH:6]=3)=[O:44])=[C:32]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[N:33]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[CH:21]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 21088585HCID 21088585, compoundHCID 21088749HCID 21088749, compound

Product 1

HCID 21088561HCID 21088561, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the obtained hydrochloride (100 mg), 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propionic acid (30 mg), 1-hydroxy-7-aza-1H-1,2,3-benzotriazole (22 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (29 mg) and N,N-dimethylformamide (0.5 ml) was stirred overnight at room temperature. To the reaction mixture was added 0.1N aqueous hydrochloric acid solution (1 ml) and the reaction mixture was extracted with ethyl acetate (2 ml). The organic layer was concentrated, introduced into preparative HPLC and purified to give 3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]-N-{4-[(diethylphosphono)(difluoro)methyl]phenyl}propionamide (51.4 mg, yield 50%). Recrystallization from ethyl acetate-isopropyl ether gave yellow prism crystals. melting point: 155–156° C.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (2 ml)
  2. concentrationThe organic layer was concentrated
  3. additionintroduced into preparative HPLC
  4. custompurified

Sources & evidence

ORD record
ord-8cc8cd06b1f34909b8eae18a7d4a2930
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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