Hydrochloric Acid → dimethyl 4-{[(2E)-3-[5-(3-furyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl]amino}benzylphosphonate

HRID 30724Notes

Reaction equation

HRID 30724 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.[O:15]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][C:21]=2/[CH:26]=[CH:27]/[C:28](O)=[O:29])=[CH:16]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.Cl>CN(C)C=O>[O:15]1[CH:19]=[CH:18][C:17]([C:20]2[N:24]([CH3:25])[N:23]=[CH:22][C:21]=2/[CH:26]=[CH:27]/[C:28]([NH:1][C:2]2[CH:14]=[CH:13][C:5]([CH2:6][P:7](=[O:12])([O:8][CH3:9])[O:10][CH3:11])=[CH:4][CH:3]=2)=[O:29])=[CH:16]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 12843961Dimethyl [(4-aminophenyl)methyl]phosphonateHCID 69209210(2E)-3-[5-(3-furyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid

Product 1

HCID 86602529dimethyl 4-{[(2E)-3-[5-(3-furyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl]amino}benzylphosphonateYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of dimethyl 4-aminobenzylphosphonate (258 mg), (2E)-3-[5-(3-furyl)-1-methyl-1H-pyrazol-4-yl]acrylic acid (218 mg), 1-hydroxy-1H-1,2,3-benzotriazole hydrate (184 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (230 mg) and N,N-dimethylformamide (8 mL) was stirred overnight at room temperature. The reaction mixture was poured into a 0.5N aqueous hydrochloric acid solution, and the mixture was 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 ethyl acetate-hexane to give dimethyl 4-{[(2E)-3-[5-(3-furyl)-1-methyl-1H-pyrazol-4-yl]prop-2-enoyl]amino}benzylphosphonate (123 mg, yield 30%) as colorless prism crystals. melting point: 176-177° C.

Workup

  1. extractionthe mixture was extracted 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 ethyl acetate-hexane

Sources & evidence

ORD record
ord-7137011b6b3f43738e2a2425c1cdb771
Source dataset
uspto-grants-2008_09
Patent number
US07423159B2

Reaction notes

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