1-Hydroxybenzotriazole → HCID 10094966, compound

HRID 1991076Notes

Reaction equation

HRID 1991076 reaction equation
[CH2:1]([C@H:3]1[NH:8][CH2:7][CH2:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH2:4]1)[CH3:2].C1C=CC2N(O)N=NC=2C=1.[C:27]([NH:30][C:31]1[CH:36]=[C:35]([Cl:37])[CH:34]=[CH:33][C:32]=1/[CH:38]=[CH:39]/[C:40](O)=[O:41])(=[O:29])[CH3:28]>C(Cl)Cl>[Cl:37][C:35]1[CH:34]=[CH:33][C:32](/[CH:38]=[CH:39]/[C:40]([N:8]2[CH2:7][CH2:6][N:5]([CH2:9][C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)[CH2:4][C@H:3]2[CH2:1][CH3:2])=[O:41])=[C:31]([NH:30][C:27](=[O:29])[CH3:28])[CH:36]=1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 45095470HCID 45095470, compoundHCID 68538268HCID 68538268, compound

Product 1

HCID 10094966HCID 10094966, compoundYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(R)-3-Ethyl-1-(4-fluorobenzyl)-piperazine (44.4 mg, 0.2 mmol), EDC1 (76 mg, 0.4 mmol), HOBT (55 mg, 0.4 mmol) and (E)-3-(2-Acetylamino-4-chloro-phenyl)-acrylic acid (47.8 mg, 0.2 mmol) were dissolved in 5 ml DCM and this mixture was stirred at room temperature overnight. The mixture was diluted with 50 ml DCM and extracted 3 times with water and once with saturated sodium chloride solution. The title compound, purified by chromatography (SiO2, ethyl acetate/MeOHINH3conc, 98/2/0.2) and was isolated as pale solid (81 mg, 91%)

Workup

  1. extractionextracted 3 times with water
  2. customThe title compound, purified by chromatography (SiO2, ethyl acetate/MeOHINH3conc, 98/2/0.2)

Sources & evidence

ORD record
ord-9285772bd5fd43d694fc72d33089527f
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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