Benzoyl chloride, 3-chloro- → HCID 58337514, compound

HRID 1887450Notes

Reaction equation

HRID 1887450 reaction equation
[CH3:1][N:2]([C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([NH2:9])[CH:4]=1.CCN(C(C)C)C(C)C.[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29](Cl)=[O:30]>C(Cl)Cl>[Cl:25][C:26]1[CH:27]=[C:28]([CH:32]=[CH:33][CH:34]=1)[C:29]([NH:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([N:2]([CH3:1])[C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:4]=1)=[O:30]

Participants

5

Reactant 3

HCID 69252Benzoyl chloride, 3-chloro-HCID 81531DiisopropylethylamineHCID 58337609HCID 58337609, compound

Product 1

HCID 58337514HCID 58337514, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Compound 17 (25 mg, 0.13 mmol, 1.0 eq) was dissolved in CH2Cl2 (1 mL) and DIEA (24 μL, 0.14 mmol, 1.1 eq) was added and the reaction stirred for 5 min. 3-Chlorobenzoyl chloride (16.1 μL, 0.125 mmol, 1.00 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 30 mg (71%) of the title compound as a light-yellow solid: 1H NMR (400 MHz, CDCl3) δ 10.44 (s, 1H), 8.36-8.15 (m, 2H), 7.98 (s, 1H), 7.89 (d, J=7.8 Hz, 1H), 7.76-7.72 (m, 1H), 7.71-7.60 (m, 4H), 7.56 (t, J=7.9 Hz, 1H), 7.44 (t, J=8.1 Hz, 1H), 7.02 (d, J=8.0 Hz, 1H), 3.36 (s, 3H); ES-MS [M+1]+: 338.2.

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-64927e69993d4a2ba08bbb7583e7f4a7
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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