1,2-Dichloroethane → HCID 16041232, compound

HRID 418610Notes

Reaction equation

HRID 418610 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:30])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:20][CH:19]=3)[S:17][C:10]=12.[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].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([NH:30][C:42](=[O:43])[CH2:41][C:40]([NH:39][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=2[O:32][CH3:31])=[O:45])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[CH:15]=[C:16]([C:18]3[CH:19]=[CH:20][C:21]([CH2:24][N:25]4[CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:22][CH:23]=3)[S:17][C:10]=12

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 12664594N-(2-Methoxy-phenyl)-malonamic acidHCID 58790325HCID 58790325, compound

Product 1

HCID 16041232HCID 16041232, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of amine 54 (260 mg, 0.57 mmol, crude) in DMF (6 mL), were added acid 27 (108 mg, 0.52 mmol) and HOBt (77 mg, 0.57 mmol). After stirring for 5 min, EDC (120 mg, 0.63 mmol) was added, and the reaction mixture was stirred at room temperature for additional 4 hours and concentrated under reduced pressure. The residue was purified by preparative HPLC (column Aquasil C-18, gradient, MeOH 60% to MeOH 95% in water) to afford title compound 48 (160 mg, 46% yield) as a white solid. 1H NMR (DMSO-d6) δ (ppm): 10.87 (bs, 1H), 10.75 (s, 1H), 9.62 (s, 1H), 8.60 (d. 1H), 8.17 (s, 1H), 8.02 (m, 3H), 7.89 (d, 1H), 7.74 (d, 2H), 7.51 (m, 1H), 7.05 (m, 2H), 6.90 (t, 1H), 6.79 (d, 1H), 4.39 (d, 1H), 6.57 (d, 1H), 3.84 (s, 2H), 3.69 (s, 2H), 3.35 (m, 2H), 3.06 (m, 3H), 2.00 (m, 2H), 1.87 (m, 2H). MS (m/z): 610.0 (M+H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for additional 4 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC (column Aquasil C-18, gradient, MeOH 60% to MeOH 95% in water)

Sources & evidence

ORD record
ord-7d61b17b628f4be38e33e78b94d189f8
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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