1-Hydroxybenzotriazole → HCID 58011902, compound

HRID 660939Notes

Reaction equation

HRID 660939 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:19]3[CH2:21][CH2:20]3)[C:10](=[O:18])[N:11]([CH:13]([CH3:17])[C:14](O)=[O:15])[CH:12]=2)=[CH:4][CH:3]=1.[F:22][C:23]([F:33])([F:32])[C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][NH2:28].CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:19]3[CH2:21][CH2:20]3)[C:10](=[O:18])[N:11]([CH:13]([CH3:17])[C:14]([NH:28][CH2:27][C:26]3[CH:29]=[CH:30][CH:31]=[C:24]([C:23]([F:22])([F:32])[F:33])[CH:25]=3)=[O:15])[CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 759623-(Trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58011648HCID 58011648, compound

Product 1

HCID 58011902HCID 58011902, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

50 mg (0.163 mmol) of 2-(4-[4-chlorophenyl]-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl)-propionic acid from Example 131A, 31.4 mg (0.179 mmol) of 3-trifluoromethylbenzylamine, 40.6 mg (0.212 mmol) of EDC hydrochloride and 26.4 mg (0.196 mmol) of HOBt are dissolved in 1 ml of dry dimethylformamide and stirred overnight at room temperature. The mixture is partitioned between water and dichloromethane, and the separated organic phase is dried over sodium sulphate and concentrated. The crude product that remains is purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 100:1→50:1). 42 mg (56% of theory) of the target compound are thus obtained.

Workup

  1. customThe mixture is partitioned between water and dichloromethane
  2. dry with materialthe separated organic phase is dried over sodium sulphate
  3. concentrationconcentrated
  4. customThe crude product that remains is purified by flash chromatography on silica gel (eluent
  5. custom42 mg (56% of theory) of the target compound are thus obtained

Sources & evidence

ORD record
ord-901b655ca2dd4760881d87947794c65e
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

Loading…