2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 67237046, compound

HRID 1471028Notes

Reaction equation

HRID 1471028 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([NH:15][C:16]1[CH:17]=[C:18]([CH:32]2[N:36]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([CH3:46])([CH3:45])[CH3:44])=[CH:39][CH:38]=3)[CH:35]([C:47]3[CH:52]=[CH:51][C:50]([NH:53][C:54]([C@@H:56]4[CH2:60][CH2:59][CH2:58][N:57]4[C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])=[O:55])=[CH:49][CH:48]=3)[CH2:34][CH2:33]2)[CH:19]=[CH:20][C:21]=1[NH:22]CC1C=CC(OC)=CC=1)=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl.O>[NH2:22][C:21]1[CH:20]=[CH:19][C:18]([CH:32]2[N:36]([C:37]3[CH:38]=[CH:39][C:40]([C:43]([CH3:45])([CH3:44])[CH3:46])=[CH:41][CH:42]=3)[CH:35]([C:47]3[CH:48]=[CH:49][C:50]([NH:53][C:54]([C@@H:56]4[CH2:60][CH2:59][CH2:58][N:57]4[C:61]([O:63][C:64]([CH3:67])([CH3:66])[CH3:65])=[O:62])=[O:55])=[CH:51][CH:52]=3)[CH2:34][CH2:33]2)=[CH:17][C:16]=1[NH:15][C:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[O:14]

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 86649118HCID 86649118, compound

Product 1

HCID 67237046HCID 67237046, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product from Example 179F (1.06 g, 1.16 mmol) in CH2Cl2 (40 mL) and H2O (2 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (0.316 g, 1.393 mmol) in several portions. The mixture was stirred at rt for 20 min and was washed with saturated. aq. NaHCO3. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography on silica gel using a solvent gradient of 0-25% EtOAc in hexane to give the title compound (0.53 g, 57%).

Workup

  1. washwas washed with saturated
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by column chromatography on silica gel using a solvent gradient of 0-25% EtOAc in hexane

Sources & evidence

ORD record
ord-1007bd11cc794deea6894efeddf78325
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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