Pyridine → HCID 19076549, compound

HRID 234536Notes

Reaction equation

HRID 234536 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].FC(F)(F)C(O)=O.[NH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[Cl:53])[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=2)[N:21]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[O:40])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:20]1=[O:46].N1C=CC=CC=1>C(Cl)Cl>[C:1]([NH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][C:48]=2[Cl:53])[C:27]2[C:22](=[CH:23][CH:24]=[C:25]([Cl:28])[CH:26]=2)[N:21]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([NH:38][C:39]([N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])=[O:40])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:20]1=[O:46])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chloride2×HCID 19076394HCID 19076394, compound

Product 1

HCID 19076549HCID 19076549, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 0.034 g of acetyl chloride in 0.5 ml of DCM is added at RT to a solution of 0.276 g of the compound obtained in EXAMPLE 199, in the form of the free base, and 2 ml of pyridine in 2 ml of DCM and the mixture is stirred for 1 hour. A further 0.034 g of acetyl chloride is added and the reaction mixture is stirred for 30 minutes at RT and concentrated under vacuum. The residue is taken up with AcOEt, the organic phase is washed with water and with a saturated solution of NaCl and dried over sodium sulfate and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (50/50; v/v) as the eluent to give 0.14 g of the expected product after crystallization from a DCM/iso ether mixture. M.p.=195°-198° C.

Workup

  1. stirringthe reaction mixture is stirred for 30 minutes at RT
  2. concentrationconcentrated under vacuum
  3. washthe organic phase is washed with water and with a saturated solution of NaCl
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is evaporated off under vacuum
  6. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (50/50; v/v) as the eluent

Sources & evidence

ORD record
ord-a6d38563978043368c494a31f4a82e3e
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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