1,2-Dichloroethane → HCID 72375749, compound

HRID 2173438Notes

Reaction equation

HRID 2173438 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([OH:16])=O)[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[N:11][N:10]=[N:9]1.[N:17]1([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)[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH2:13][C:14]([N:20]2[CH2:21][CH2:22][N:17]([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)[CH2:18][CH2:19]2)=[O:16])[CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[N:11][N:10]=[N:9]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 595686715-[2-(piperazin-1-yl)ethyl]-2-benzofuran-1(3H)-oneHCID 67517239HCID 67517239, compound

Product 1

HCID 72375749HCID 72375749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of [3-fluoro-4-(1H-tetrazol-1-yl)phenyl]acetic acid (0.68 mmol) in 10 mL of anhydrous DCM was added 5-(2-piperazin-1-ylethyl)-2-benzofuran-1(3H)-one (191 mg, 0.68 mmol), EDC (200 mg, 1.01 mmol), HOBt (136 mg, 1.01 mmol), TEA (341 mg, 3.38 mmol) was stirred at ambient temperature overnight. The mixture was added DCM, washed with brine, the organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified via prep-TLC to give the title compound. 1H-NMR (400 MHz, CDCl3) δ ppm 8.84 (s, 1H), 7.82 (d, J=7.8 Hz, 1H), 7.31˜737 (m, 3H), 7.11˜7.19 (m, 2H), 5.29 (s, 2H), 3.59 (s, 2H), 3.49˜3.52 (m, 2H), 3.37˜3.4 (m, 2H), 2.89˜2.93 (m, 2H), 2.64˜2.68 (m, 2H), 2.4˜2.45 (m, 4H).

Workup

  1. washwashed with brine
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified via prep-TLC

Sources & evidence

ORD record
ord-0c8a36f661ce4f6ab5a7e497ca1420ba
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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