Hydrochloric Acid → HCID 10481431, compound

HRID 1991069Notes

Reaction equation

HRID 1991069 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5](/[CH:10]=[CH:11]/[C:12]([OH:14])=O)=[C:4]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:3]=1.[F:20][C:21]1[CH:35]=[CH:34][C:24]([CH2:25][N:26]2[CH2:31][C@H:30]([CH3:32])[NH:29][CH2:28][C@H:27]2[CH3:33])=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][C:5](/[CH:10]=[CH:11]/[C:12]([N:29]2[CH2:28][C@H:27]([CH3:33])[N:26]([CH2:25][C:24]3[CH:34]=[CH:35][C:21]([F:20])=[CH:22][CH:23]=3)[CH2:31][C@H:30]2[CH3:32])=[O:14])=[C:4]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23405839(2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazineHCID 58683755HCID 58683755, compound

Product 1

HCID 10481431HCID 10481431, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(E)-3-(4-Chloro-2-methanesulfonylamino-5-methoxyphenyl)-acrylic acid (100 mg; 0.32 mmol), (2R,5S)-1-(4-fluorobenzyl)-2,5-dimethylpiperazine (Mavunkel, Babu J. et al., WO 00171535) (73 mg; 0.32 mmol) and EDCl.HCl (75 mg, 0.39 mmol), HOBt (5 mg; 0.03 mmol) were dissolved in DMF (2 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 yield the title compound as yellow foam (135 mg; 81%)

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)

Sources & evidence

ORD record
ord-24586c25cb024323bf6566be3c0ef81f
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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