1-Amino-2-propanol → HCID 178468299, compound

HRID 1797010Notes

Reaction equation

HRID 1797010 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([C@H:13]3[CH2:18][CH2:17][C@H:16]([C:19]([OH:21])=O)[CH2:15][CH2:14]3)[NH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[OH:22][CH:23]([CH3:26])[CH2:24][NH2:25].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C.O>[OH:22][CH:23]([CH3:26])[CH2:24][NH:25][C:19]([C@H:16]1[CH2:15][CH2:14][C@H:13]([C:10]2[NH:11][CH:12]=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=3)[N:9]=2)[CH2:18][CH2:17]1)=[O:21]

Participants

6

Reactant 3

HCID 41-Amino-2-propanolHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 178525697HCID 178525697, compound

Product 1

HCID 178468299HCID 178468299, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The solution of trans-4-[4-(3-bromo-phenyl)-1H-imidazol-2-yl]-cyclohexyl-carboxylic acid (1.22 mmol), 2-hydroxy-propylamine(3.65 mmol) and BOP (1.22 mmol) in DMF (6 mL) was stirred overnight at room temperature. The mixture was diluted with water, extracted with EtOAc, washed with saturated NaHCO3, dried over Na2SO4, and concentrated under vacuum. The residue was purified with flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH) to give trans-4-[4-(3-bromo-phenyl)-1H-imidazol-2-yl]-cyclohexane-carboxylic acid (2-hydroxy-propyl) amide.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with saturated NaHCO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified with flash chromatography (90:10:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-c5e034eb0dac4b45b913a031aac82f5b
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

Loading…