Dichloromethane → HCID 67517817, compound

HRID 2173443Notes

Reaction equation

HRID 2173443 reaction equation
[CH:1]([C:3]1[CH:8]=[C:7]([N:9]2[CH:13]=[N:12][N:11]=[N:10]2)[CH:6]=[CH:5][C:4]=1[CH2:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][C:25]2[CH:34]=[CH:33][C:28]3[C:29](=[O:32])[O:30][CH2:31][C:27]=3[CH:26]=2)[CH2:19][CH2:18]1)=[O:16])=[CH2:2].[CH2:35](Cl)Cl>CCOCC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:1]1([C:3]2[CH:8]=[C:7]([N:9]3[CH:13]=[N:12][N:11]=[N:10]3)[CH:6]=[CH:5][C:4]=2[CH2:14][C:15]([N:17]2[CH2:18][CH2:19][N:20]([CH2:23][CH2:24][C:25]3[CH:34]=[CH:33][C:28]4[C:29](=[O:32])[O:30][CH2:31][C:27]=4[CH:26]=3)[CH2:21][CH2:22]2)=[O:16])[CH2:35][CH2:2]1

Participants

5

Reactant 2

HCID 6344DichloromethaneHCID 67517720HCID 67517720, compound

Product 1

HCID 67517817HCID 67517817, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 3283Diethyl EtherSolvent

Procedure

A solution of 5-[2-(4-{[2-ethenyl-4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one (40 mg, 0.08 mmol) in 5 mL of DCM was added a solution of CH2N2 in 2 mL Et2O and Pd(OAc)2 (10 mg) at 0° C. The mixture was stirred at room temperature overnight. The reaction mixture was filtrated and purified by prep-TLC to afford 5-[2-(4-{[2-cyclopropyl-4-(1H-tetrazol-1-yl)phenyl]acetyl}piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one. 1H-NMR (400 MHz, CDCl3) δ ppm 9.0 (s, 1H), 7.76˜7.78 (m, 1H), 7.26˜7.4 (in, 5H), 5.22 (s, 2H), 3.88 (s, 2H), 3.49˜3.66 (m, 4H), 2.83˜2.93 (m, 2H), 2.6˜2.62 (m, 2H), 2.38˜2.48 (m, 4H), 2.0 (s, 1H), 0.94˜0.98 (m, 2H), 0.66˜0.68 (m, 2H).

Workup

  1. filtrationThe reaction mixture was filtrated
  2. custompurified by prep-TLC

Sources & evidence

ORD record
ord-d710569c168647d6bf4909dd458a6b6a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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