1,2-Dichloroethane → HCID 68774407, compound

HRID 1175611Notes

Reaction equation

HRID 1175611 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=O)[CH:6]=[CH:7][C:8]=1[C:9]1[C:13]([CH3:14])=[CH:12][S:11][CH:10]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.[CH2:35]([NH2:39])[CH:36]([CH3:38])[CH3:37]>CN(C=O)C>[CH2:35]([NH:39][C:16](=[O:18])[C:15]([C:5]1[CH:6]=[CH:7][C:8]([C:9]2[C:13]([CH3:14])=[CH:12][S:11][CH:10]=2)=[C:3]([O:2][CH3:1])[CH:4]=1)([CH3:20])[CH3:19])[CH:36]([CH3:38])[CH3:37]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6558IsobutylamineHCID 757711-HydroxybenzotriazoleHCID 68778118HCID 68778118, compound

Product 1

HCID 68774407HCID 68774407, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-methoxy-4-(4-methylthiophen-3-yl)phenyl)-2-methylpropanoic acid (example 35b) (630 mg, 2.2 mmol) in DMF (7 mL) were added HOBt (297 mg, 2.2 mmol), EDC (434 mg, 2.2 mmol) and isobutyl amine (214 μL, 2.2 mmol). The mixture was stirred at room temperature overnight and evaporated under reduced pressure. The residue was dissolved in EtOAc and successively washed with water, 10% citric acid, sat. NaHCO3 and water, dried over MgSO4, filtered and evaporated. The residue was chromatographed on silica gel (30% EtOAc-hexanes) to give 190 mg (37%) of N-isobutyl-2-(3-methoxy-4-(4-methylthiophen-3-yl)phenyl)-2-methylpropanamide. 1H NMR (400 MHz, dMSO): δ 0.73-0.75 (d, 6H), 1.48 (s, 6H), 1.69-1.72 (m, 1H), 2.00 (s, 3H), 2.49-2.50 (m, 2H), 3.71 (s, 3H), 6.91-6.94 (m, 2H), 7.08-7.10 (d, 1H), 7.18 (s, 1H), 7.24-7.25 (d, 1H), 7.34-7.35 (t, 1H).

Workup

  1. customevaporated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washsuccessively washed with water, 10% citric acid, sat. NaHCO3 and water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was chromatographed on silica gel (30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-12d83aab9e0b4c94b4733cf7f95bbb19
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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