Hydrochloric Acid → HCID 10390122, compound

HRID 1991066Notes

Reaction equation

HRID 1991066 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([Cl:11])[C:8]([O:12][CH3:13])=[CH:7][C:6]=1/[CH:14]=[CH:15]/[C:16]([OH:18])=O)(=[O:3])[CH3:2].[F:19][C:20]1[CH:34]=[CH:33][C:23]([CH2:24][N:25]2[CH2:30][C@H:29]([CH3:31])[NH:28][CH2:27][C@H:26]2[CH3:32])=[CH:22][CH:21]=1.CCN=C=NCCCN(C)C.Cl.Cl>CN(C=O)C>[Cl:11][C:9]1[C:8]([O:12][CH3:13])=[CH:7][C:6](/[CH:14]=[CH:15]/[C:16]([N:28]2[CH2:27][C@H:26]([CH3:32])[N:25]([CH2:24][C:23]3[CH:33]=[CH:34][C:20]([F:19])=[CH:21][CH:22]=3)[CH2:30][C@H:29]2[CH3:31])=[O:18])=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23405839(2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazineHCID 59128618HCID 59128618, compound

Product 1

HCID 10390122HCID 10390122, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-3-(2-Acetylamino-4-chloro-5-methoxyphenyl)-acrylic acid (100 mg; 0.37 mmol), (2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine (Mavunkel, Babu J. et al., WO 00/71535) (83 mg; 0.37 mmol) and EDCl.HCl (85 mg, 0.44 mmol) were dissolved in DMF (3 ml) and stirred over night. The reaction mixture was evaporated, taken up in 2N Na2CO3 and extracted with EtOAc three times. The combined organic phases were evaporated and purified via chromatography (SiO2 acetone/hexanes 3/7 to 4/6) to yield the title compound as colorless crystals (97 mg; 55%).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with EtOAc three times
  3. customThe combined organic phases were evaporated
  4. custompurified via chromatography (SiO2 acetone/hexanes 3/7 to 4/6)

Sources & evidence

ORD record
ord-7850bbef1e50435a82504e2e7157f41e
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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