Acrylic Acid → HCID 57801513, compound

HRID 2101494Notes

Reaction equation

HRID 2101494 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1.[C:25]([OH:29])(=[O:28])[CH:26]=[CH2:27]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:21]=[C:22]([Cl:24])[CH:23]=1)[CH2:5][N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[CH2:11][N:12]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=1)[CH2:27][CH2:26][C:25]([OH:29])=[O:28]

Participants

4

Reactant 2

HCID 6581Acrylic AcidHCID 11951591HCID 11951591, compound

Product 1

HCID 57801513HCID 57801513, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of [1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amine (see Example 6), (113 mg, 0.31 mmol), acrylic acid (23 mg, 0.33 mmol) and benzene (4 mL) was heated to reflux for 14 h. The solvent was evaporated in vacuo to afford crude 3-[[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethyl]-(3-fluoro-benzyl)-amino]-propionic acid. To a mixture of this acid (135 mg, 0.31 mmol), isonipecotamide (44 mg, 0.35 mmol), 1-hydroxybenzotriazole (45 mg, 0.33 mmol) and CH2Cl2 (1 mL) at 0° C. was added a solution of dicyclohexylcarbodiimide (68 mg, 0.33 mmol) in CH2Cl2 (0.5 mL). The mixture was stirred at ambient temperature for 14 h and then concentrated in vacuo. The residue was purified by column chromatography (silica gel, 20:1 to 10:1 CH2Cl2/MeOH) to provide the title compound (86 mg, 51%) as a white solid: ESI MS m/z 546 [C27H30Cl2FN5O2+H]+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 14 h
  3. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-a70b44ce23ba406cbe5aa2bc12eff7a6
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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