1-Hydroxybenzotriazole → HCID 58012279, compound

HRID 660938Notes

Reaction equation

HRID 660938 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH:18]3[CH2:20][CH2:19]3)[C:10](=[O:17])[N:11]([CH2:13][C:14]([OH:16])=O)[CH:12]=2)=[CH:4][CH:3]=1.[C:21]1([C@H:31]([NH2:33])[CH3:32])[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.CCN=C=NCCCN(C)C.Cl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH:18]3[CH2:20][CH2:19]3)[C:10](=[O:17])[N:11]([CH2:13][C:14]([NH:33][C@H:31]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[CH:24]=[CH:23][CH:22]=3)[CH3:32])=[O:16])[CH:12]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 2724264(+)-1-(1-Naphthyl)ethylamineHCID 58011744HCID 58011744, compound

Product 1

HCID 58012279HCID 58012279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (0.512 mmol) of [4-(4-chlorophenyl)-3-cyclopropyl-2-oxo-2,3-dihydro-1H-imidazol-1-yl]-acetic acid from Example 130A, 96.5 mg (0.564 mmol) of (1R)-1-(1-naphthyl)ethylamine, 128 mg (0.67 mmol) of EDC hydrochloride and 83.1 mg (0.62 mmol) of HOBt are dissolved in 2 ml of dry DMF and stirred overnight at room temperature. The crude product is purified by flash chromatography on silica gel (eluent: first dichloromethane, then dichloromethane/methanol 100:1). The target compound is obtained in a yield of 172 mg (75% of theory).

Workup

  1. customThe crude product is purified by flash chromatography on silica gel (eluent
  2. customThe target compound is obtained in a yield of 172 mg (75% of theory)

Sources & evidence

ORD record
ord-3647ef7c6098419eba7fa96a15106015
Source dataset
uspto-grants-2011_12
Patent number
US08084481B2

Reaction notes

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