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1,2-Dichloroethane → HCID 67517720, compound

HRID 2173442
Notes
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Reaction equation

HRID 2173442 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]([OH:17])=O)=[CH2:2].Cl.[N:19]1([CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][C:30]3[C:31](=[O:34])[O:32][CH2:33][C:29]=3[CH:28]=2)[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[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:22]1[CH2:23][CH2:24][N:19]([CH2:25][CH2:26][C:27]2[CH:36]=[CH:35][C:30]3[C:31](=[O:34])[O:32][CH2:33][C:29]=3[CH:28]=2)[CH2:20][CH2:21]1)=[O:17])=[CH2:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 666467325-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one hydrochlorideHCID 67517397HCID 67517397, compound

Product 1

HCID 67517720HCID 67517720, compound

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
2×

Procedure

A solution of [2-ethenyl-4-(1H-tetrazol-1-yl)phenyl]acetic acid (43 mg, 0.19 mmol) in 10 mL of anhydrous DCM was added 5-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-one hydrochloride (53 mg, 0.19 mmol), EDC (56 mg, 0.28 mmol), HOBt (38 mg, 0.28 mmol), TEA (115 mg, 1.14 mmol) and then stirred at ambient temperature overnight. Then DCM was added and then mixture was washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to afford 5-[2-(4-{[2-ethenyl-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), 7.75˜7.78 (m, 2H), 7.48˜7.51 (m, 1H), 7.26˜7.31 (m, 3H), 6.76˜6.84 (rn, 1H), 5.7 (d, J=17.2 Hz, 1H), 5.44 (d, J=10.9 Hz, 1H), 5.22 (s, 2H), 3.75 (s, 2H), 3.6˜3.65 (m, 2H), 3.45˜3.48 (m, 2H), 2.86˜2.9 (m, 2H), 2.59˜2.64 (m, 2H), 2.41˜2.5 (m, 4H).

Workup

  1. washmixture was washed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

Sources & evidence

ORD record
ord-dc8c9a94e1714875b6591579fea2450b
Source dataset
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09056859B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes