Potassium Carbonate → HCID 86681610, compound

HRID 571187Notes

Reaction equation

HRID 571187 reaction equation
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:42])[CH:5]=[C:6]([Cl:41])[C:7]=1[CH2:8][C@@H:9]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([F:35])[F:34])=[C:28]([O:36][CH2:37][CH:38]2[CH2:40][CH2:39]2)[CH:27]=1)[O:10][C:11](=[O:25])[CH2:12][N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][C:15](=[O:23])[C:14]1=[O:24].Cl[CH2:44][CH2:45][N:46]1[CH2:51][CH2:50][O:49][CH2:48][CH2:47]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:42])[CH:5]=[C:6]([Cl:41])[C:7]=1[CH2:8][C@@H:9]([C:26]1[CH:31]=[CH:30][C:29]([O:32][CH:33]([F:35])[F:34])=[C:28]([O:36][CH2:37][CH:38]2[CH2:39][CH2:40]2)[CH:27]=1)[O:10][C:11](=[O:25])[CH2:12][N:13]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]([CH2:44][CH2:45][N:46]2[CH2:51][CH2:50][O:49][CH2:48][CH2:47]2)[C:15](=[O:23])[C:14]1=[O:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 86681609HCID 86681609, compound

Product 1

HCID 86681610HCID 86681610, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(2,3-dioxo-3,4-dihydroquinoxalin-1(2H)-yl)acetoxy)-ethyl)pyridine 1-oxide (70 mg, 0.112 mmol) dissolved in DMF (1 mL), 4-(2-chloroethyl)morpholine (34 mg, 0.225 mmol) and potassium carbonate (23 mg, 0.169 mmol) were added. The mixture was stirred at 40 degrees for 5 hours. The mixture was then diluted with H2O (10 mL) and the aqueous phase extracted with AcOEt (2×3 mL). The organic phase was washed with brine (10 ml), dried over Na2SO4 and the solvent was evaporated, to yield 22 mg of the title compound (yield 37%). MS/ESI+ 735.4 [MH]+; 1H NMR (400 MHz, acetone) δ ppm 8.01 (s, 2H), 7.53-7.62 (m, 1H), 7.28-7.39 (m, 1H), 7.09-7.24 (m, 3H), 6.99-7.07 (m, 2H), 6.93 (t, J=75.00 Hz, 1H), 5.97-6.21 (m, 1H), 5.10-5.21 (m, 1H), 4.76-4.84 (m, 1H), 4.36-4.56 (m, 2H), 3.89-4.12 (m, 2H), 3.61 (m, 4H), 3.35-3.51 (m, 1H), 3.15-3.27 (m, 1H), 2.76-2.80 (m, 2H), 2.52-2.65 (m, 4H), 1.25-1.39 (m, 1H), 0.55-0.68 (m, 2H), 0.37-0.52 (m, 2H).

Workup

  1. extractionthe aqueous phase extracted with AcOEt (2×3 mL)
  2. washThe organic phase was washed with brine (10 ml)
  3. dry with materialdried over Na2SO4
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-71a850e40ac6475f9fccff8123af6953
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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