Pyridine → HCID 11569825, compound

HRID 2425098Notes

Reaction equation

HRID 2425098 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:34])[C:13]2[O:19][C:18]3[C:20]([Cl:30])=[CH:21][C:22]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:32])(=[O:31])[C:14]=2[CH:33]=1)=[O:9].N1C=CC=CC=1>ClCCl>[CH3:6][O:7][C:8]([C:10]1[CH:11]=[C:12]([CH3:34])[C:13]2[O:19][C:18]3[C:20]([Cl:30])=[CH:21][C:22]([N:24]4[CH2:25][CH2:26][N:27]([S:1]([CH3:4])(=[O:3])=[O:2])[CH2:28][CH2:29]4)=[CH:23][C:17]=3[CH2:16][S:15](=[O:31])(=[O:32])[C:14]=2[CH:33]=1)=[O:9]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 115410724-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cyclo heptene-8-carboxylic acid methyl ester

Product 1

HCID 11569825HCID 11569825, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Mesyl chloride (0.16 mL, 2.059 mmol) was added to a solution of 4-Chloro-6-methyl-10,10-dioxo-2-piperazin-1-yl-10,11-dihydro-5-oxa-10lambda*6*-thia-dibenzo[a,d]cycloheptene-8-carboxylic acid methyl ester (free base of example 16, 0.3 g, 0.687 mmol) in dichloromethane (20 mL) and stirred at 20° C. for 10 min. To this pyridine (0.3 mL, 4.12 mmol) was added and the reaction mixture was stirred further for 5 h. The reaction mixture was washed using aqueous hydrochloric acid 10% (15 mL), water and then brine solution. Solvent was removed and the crude product obtained was purified by column chromatography (silica gel, 1% methanol in chloroform) to obtain the title compound. Yield: 0.14 g, (38.45%); 1H NMR (DMSO-d6, 300 MHz): δ 2.63 (s, 3H, CH3), 2.90 (s, 3H, CH3), 3.22 (s, 4H, 2CH2); 3.31 (s, 4H, CH2); 3.85 (s, 3H, OCH3); 5.16 (s, 2H, CH2), 7.13 (d, 1H, Ar), 7.18 (s, 1H, Ar), 8.09 (t, 1H, Ar), 8.15 (d, 1H, Ar); MS: m/e (ES+) 515 (M+1); analysis: C21H23ClN2O7S2.H2O requires C, 47.32; H, 4.73; N, 5.26; Cl, 6.65; S, 12.03. found: C, 46.86; H, 4.18; N, 4.96; Cl, 7.11; S, 12.57%.

Workup

  1. stirringthe reaction mixture was stirred further for 5 h
  2. washThe reaction mixture was washed
  3. customSolvent was removed
  4. customthe crude product obtained
  5. customwas purified by column chromatography (silica gel, 1% methanol in chloroform)

Sources & evidence

ORD record
ord-1641b857386746c6845015759a6ceea6
Source dataset
uspto-grants-2011_06
Patent number
US07964631B2

Reaction notes

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