1,2-Dichloroethane → HCID 58790092, compound

HRID 2193804Notes

Reaction equation

HRID 2193804 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]3[CH:13]=[C:14]([C:16]4[CH:17]=[CH:18][C:19](=[O:27])[N:20]([CH2:22][CH2:23][N:24]([CH3:26])[CH3:25])[CH:21]=4)[S:15][C:8]=23)=[C:4]([F:30])[CH:3]=1.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[NH:39][C:40](=[O:45])[CH2:41][C:42](O)=[O:43].OC1C2N=NNC=2C=CC=1.C(Cl)CCl.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH3:26][N:24]([CH3:25])[CH2:23][CH2:22][N:20]1[C:19](=[O:27])[CH:18]=[CH:17][C:16]([C:14]2[S:15][C:8]3[C:9](=[N:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]3[CH:28]=[CH:29][C:2]([NH:1][C:42](=[O:43])[CH2:41][C:40]([NH:39][C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[O:32][CH3:31])=[O:45])=[CH:3][C:4]=3[F:30])[CH:13]=2)=[CH:21]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 516892Sodium BicarbonateHCID 12664594N-(2-Methoxy-phenyl)-malonamic acidHCID 58790376HCID 58790376, compoundHCID 178418300HCID 178418300, compound

Product 1

HCID 58790092HCID 58790092, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of compound 422 (25 mg, 0.059 mmol) in DMF (0.5 mL) was added the acid 27 (25 mg, 0.12 mmol), hydroxybenzotriazole (11 mg, 0.071 mmol), then EDC (23 mg, 0.12 mmol). The reaction mixture was stirred at room temperature for 6 hours before the addition of saturated NaHCO3 (8 mL). The mixture was then extracted with dichloromethane; the extract was dried over anhydrous Na2SO4, filtered and concentrated. The residue was then purified by flash chromatography (eluent a gradient of 0 to 20% methanol in dichloromethane) to give title compound 417 as a white solid (19 mg, 53% yield). 1H NMR: (DMSO-d6) δ(ppm): 10.58 (s, 1H), 9.62 (s, 1H), 8.45 (d, J=5.6 Hz, 1H), 8.28 (d, J=2.8 Hz, 1H), 8.05 (d, J=8.4 Hz, 1H), 7.95 (dd, J=2.8, 9.6 Hz, 1H), 7.88-7.84 (m, 2H), 7.45 (t, J=8.8 Hz, 1H), 7.43-7.40 (m, 1H), 7.07-7.03 (m, 2H), 6.92-6.88 (m, 1H), 6.60 (d, J=5.6 Hz, 1H), 6.51 (d, J=9.6 Hz, 1H), 4.05 (t, J=6.0 Hz, 2H), 3.84 (s, 3H), 3.62 (s, 2H), 2.53 (t, J=6.4 Hz, 2H), 2.47 (s, 6H). MS (m/z): 308.5 ([M+2H]/2), 616.1 (M+H).

Workup

  1. extractionThe mixture was then extracted with dichloromethane
  2. dry with materialthe extract was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then purified by flash chromatography (eluent a gradient of 0 to 20% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4313cee2eff04d8dabc489997964d25f
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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