Benzoyl chloride → HCID 18700031, compound

HRID 2288604Notes

Reaction equation

HRID 2288604 reaction equation
Cl.Cl.[NH2:3][CH2:4][C:5]1[N:9]=[C:8]([C:10]2[S:14][C:13]([CH2:15][N:16]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:12][CH:11]=2)[O:7][N:6]=1.C(N(CC)CC)C.[C:30](Cl)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N:16]1([CH2:15][C:13]2[S:14][C:10]([C:8]3[O:7][N:6]=[C:5]([CH2:4][NH:3][C:30](=[O:37])[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:9]=3)=[CH:11][CH:12]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 18700052HCID 18700052, compound

Product 1

HCID 18700031HCID 18700031, compoundYield 64.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

585 mg (2.0 mmol) of the free form compound obtained in Example 8 was dissolved in 20 ml of methylene chloride, 0.6 ml (4.0 mmol) of triethylamine, 0.28 ml (2.4 mmol) of benzoyl chloride and 4-DMAP (cat.) were added, and the mixture was stirred at room temperature for 19 hours. The reaction solution was washed with water and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was subjected to a silica gel column chromatography, which was eluted with chloroform-methanol (80:1) to give 510 mg of the title compound in its free form. Using 140 mg (1.2 mmol) of fumaric acid, a 490 mg (1.24 mmol) portion of this compound was subjected to salt formation to give 348 mg of the title compound.

Workup

  1. washThe reaction solution was washed with water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated
  4. washwas eluted with chloroform-methanol (80:1)

Sources & evidence

ORD record
ord-12432872a79f4290b7e7309730c92836
Source dataset
uspto-grants-2000_07
Patent number
US06090804

Reaction notes

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