Benzoyl chloride, 3-chloro- → HCID 58337443, compound

HRID 1887442Notes

Reaction equation

HRID 1887442 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([O:9][C:10]2[CH:11]=[N:12][CH:13]=[N:14][CH:15]=2)[CH:8]=1)[NH2:5].[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20](Cl)=[O:21]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([NH:5][C:4]1[CH:6]=[C:7]([O:9][C:10]2[CH:15]=[N:14][CH:13]=[N:12][CH:11]=2)[CH:8]=[C:2]([Cl:1])[CH:3]=1)=[O:21]

Participants

5

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-HCID 58337739HCID 58337739, compound

Product 1

HCID 58337443HCID 58337443, compoundYield 6.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

Compound 9 (29 mg, 0.13 mmol, 1.0 eq) was dissolved in CH2Cl2 (1.2 mL) and DMAP (32 mg, 0.26 mmol, 2.0 eq) was added and the reaction stirred for 5 min. 3-Chlorobenzoyl chloride (23 mg, 0.13 mmol, 1.0 eq) was added and the reaction was stirred until determination of completion by LCMS. The reaction was diluted with CH2Cl2, washed with water (1×), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 2.9 mg (6%) of the title compound as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 10.54 (s, 1H), 9.07 (s, 1H), 8.75 (s, 2H), 7.96 (t, J=1.7 Hz, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.81 (t, J=1.7 Hz, 1H), 7.68-7.66 (m, 1H), 7.56 (t, J=7.9 Hz, 1H), 7.46 (t, J=2.0 Hz, 1H), 7.05 (t, J=2.0 Hz, 1H); ES-MS [M+1]+: 360.1.

Workup

  1. stirringthe reaction was stirred until determination of completion by LCMS
  2. washwashed with water (1×)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-6a3d23ec63ac435387544fe0f1a9e9a9
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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