Hydrochloric Acid → (2E)-N-[4-(dimethylphosphonomethyl)phenyl]-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide

HRID 30708Notes

Reaction equation

HRID 30708 reaction equation
[NH2:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][P:7](=[O:12])([O:10][CH3:11])[O:8][CH3:9])=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[N:26]([CH3:27])[N:25]=[CH:24][C:23]=2/[CH:28]=[CH:29]/[C:30](O)=[O:31])=[CH:18][CH:17]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl>>[CH3:11][O:10][P:7]([CH2:6][C:5]1[CH:13]=[CH:14][C:2]([NH:1][C:30](=[O:31])/[CH:29]=[CH:28]/[C:23]2[CH:24]=[N:25][N:26]([CH3:27])[C:22]=2[C:19]2[CH:20]=[CH:21][C:16]([F:15])=[CH:17][CH:18]=2)=[CH:3][CH:4]=1)([O:8][CH3:9])=[O:12]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12843961Dimethyl [(4-aminophenyl)methyl]phosphonateHCID 69208981(2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid

Product 1

HCID 86602523(2E)-N-[4-(dimethylphosphonomethyl)phenyl]-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamideYield 65%

Procedure

A mixture of dimethyl 4-aminobenzylphosphonate (0.86 g), (2E)-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid (0.74 g), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (0.61 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.77 g) and N,N-dimethylfomamide (8 ml) was stirred at room temperature overnight. The reaction mixture was poured into a 0.5N aqueous hydrochloric acid solution and extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate, and then with saturated brine, dried (MgSO4) and concentrated. The obtained solid was recrystallized from acetone-water to give (2E)-N-[4-(dimethylphosphonomethyl)phenyl]-3-[5-(4-fluorophenyl)-1-methyl-1H-pyrazol-4-yl]acrylamide (0.86 g, yield 65%) as colorless prism crystals. melting point: 209-210° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  3. dry with materialwith saturated brine, dried (MgSO4)
  4. concentrationconcentrated
  5. customThe obtained solid was recrystallized from acetone-water

Sources & evidence

ORD record
ord-a5dabef5c8464d26b2bb63562311f092
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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