1,2-Dichloroethane → HCID 16005229, compound

HRID 1175597Notes

Reaction equation

HRID 1175597 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([CH3:14])([CH3:13])[C:10](O)=[O:11])[CH:6]=[CH:5][C:4]=1[C:15]1[CH:20]=[C:19]([CH2:21][O:22][CH3:23])[CH:18]=[CH:17][CH:16]=1.C1C=CC2N(O)N=NC=2C=1.[CH2:34]([NH2:38])[CH:35]([CH3:37])[CH3:36].C(Cl)CCl>C(Cl)Cl.CN(C=O)C>[CH2:34]([NH:38][C:10](=[O:11])[C:9]([C:7]1[CH:6]=[CH:5][C:4]([C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([CH2:21][O:22][CH3:23])[CH:20]=2)=[C:3]([O:2][CH3:1])[CH:8]=1)([CH3:13])[CH3:14])[CH:35]([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 6558IsobutylamineHCID 757711-HydroxybenzotriazoleHCID 68775456HCID 68775456, compound

Product 1

HCID 16005229HCID 16005229, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-methoxy-5′-(methoxymethyl)biphenyl-4-yl)-2-methylpropanoic acid (example 27a) (315 mg, 1 mmol) in DCM (10 mL) and DMF (1 mL) were added HOBt (135 mg, 1 mmol) and isobutyl amine (98 μL, 1 mmol) followed by EDC (197 mg, 1 mmol). The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was purified by preparative RP HPLC (water-acetonitrile) to give a colorless oil that was further evaporated from EtOH (3×) and dried to yield 150 mg (41%) of the product. 1H NMR (400 MHz, dMSO): δ 0.76-0.77 (t, 3H), 1.49 (s, 6H), 1.10-1.72 (m, 1H), 2.85-2.88 (t, 2H), 3.30 (s, 3H), 3.74 (s, 3H), 4.44 (s, 2H), 6.96-6.98 (m, 2H), 7.22-7.26 (m, 2H), 7.36-7.38 (m, 4H); MS+H (370.2).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by preparative RP HPLC (water-acetonitrile)
  8. customto give a colorless oil that
  9. customwas further evaporated from EtOH (3×)
  10. customdried

Sources & evidence

ORD record
ord-5ab34bc59e6d4550be06d5de6a149b16
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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