Tris(hydroxymethyl)aminomethane → N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide

HRID 2101521Notes

Reaction equation

HRID 2101521 reaction equation
[C:1](Cl)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][O:18][C:19]1[CH:20]=[C:21]([NH2:25])[CH:22]=[CH:23][CH:24]=1.C(O)C(N)(CO)CO>C(Cl)Cl>[Cl:7][C:8]1[CH:9]=[C:10]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:11][N:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH2:17][O:18][C:19]1[CH:20]=[C:21]([NH:25][C:1](=[O:5])[CH:2]([CH3:4])[CH3:3])[CH:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 62325Isobutyryl chlorideHCID 119510703-[1-(3,5-Dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine

Product 1

HCID 11951240N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyryl chloride (11 mg, 0.1 mmol) was added to a solution of 3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenylamine (see Example 21) (30 mg, 0.09 mmol) in CH2Cl2 (1 mL). The reaction was shaken at room temperature. After 72 h, trisamine resin (79 mg, 0.1 mmol) was added and the reaction was shaken for another 4 h. The reaction was filtered and the resin was washed with CH2Cl2 (2 mL). The filtrates were combined and concentrated in vacuo. Preparative TLC (silica, 20:1 CH2Cl2:MeOH, Rf=0.4) provided N-{3-[1-(3,5-dichloro-benzyl)-1H-imidazol-2-ylmethoxy]-phenyl}-isobutyramide, 24a as a white solid (15 mg, 40%); MS m/z 418 [C21H21Cl2N3O2+H]+.

Workup

  1. stirringthe reaction was shaken for another 4 h
  2. filtrationThe reaction was filtered
  3. washthe resin was washed with CH2Cl2 (2 mL)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c7825d9b33d41ffa86333fdcfeff637
Source dataset
uspto-grants-2009_08
Patent number
US07572921B2

Reaction notes

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