1,2-Dichloroethane → HCID 58789395, compound

HRID 1175567Notes

Reaction equation

HRID 1175567 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([OH:11])=O)[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.C(Cl)CCl.[CH3:40][CH:41]([CH3:44])[CH2:42][NH2:43]>ClCCl>[F:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:12])[C:9]([NH:43][CH2:42][CH:41]([CH3:44])[CH3:40])=[O:11])[CH:5]=[CH:4][C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 3394FlurbiprofenHCID 6558IsobutylamineHCID 8471TriethylamineHCID 757711-Hydroxybenzotriazole

Product 1

HCID 58789395HCID 58789395, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2-fluorobiphenyl-4-yl)propanoic acid (Aldrich) (172.3 mg), HOBt (133.2 mg, 1.4 eq) and triethylamine (196.5 mL, 2 eq) in dichoromethane (7 mL) was added at room temparature EDC (270.4 mg, 2.0 eq). The reaction was stired at room temperature for 30 minutes and 2-methylpropan-1-amine (0.1 mL, 1.5 eq) was added. The solution was stirred overnight then diluted with dichlorometahne and washed successively with aqueous NaHCO3, water, aqoueous HCL (1N), water, dried over MGSO4, filtered and evaporated. Chromatogarphy on silica gel (eluent:ethyl acetate/hexane 1:1) afforded 170 mg of 2-(2-fluorobiphenyl-4-yl)-N-isobutylpropanamide. Yield: 80%. 1H NMR (500 MHz, CDCl3): δ 0.83-0.79 (d, 6H), 1.55-1.56 (d, 3H), 1.69-1.74 (m, 1H), 3.04-3.07 (m, 2H), 3.56-3.58 (m, 1H), 5.4 (s br, 1H), 7.11-7.16 (m, 2H), 7.37-7.46 (m, 4H), 7.53-7.55 (m, 2H).

Workup

  1. additionthen diluted with dichlorometahne
  2. washwashed successively with aqueous NaHCO3, water, aqoueous HCL (1N), water
  3. customdried over MGSO4
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-0dd8f32874b04e4688f84766489dd37e
Source dataset
uspto-grants-2010_11
Patent number
US07842324B2

Reaction notes

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