Triethylamine → HCID 18974970, compound

HRID 2393359Notes

Reaction equation

HRID 2393359 reaction equation
[NH2:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:16]3[N:12]([C:13]([CH3:17])=[N:14][N:15]=3)[C:11]3[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=3[C:9]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[N:8]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>ClCCl>[Cl:28][C:25]1[CH:24]=[CH:23][C:22]([C:9]2[C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[N:12]3[C:16]([N:7]([CH2:6][C:5]4[CH:4]=[CH:3][C:2]([NH:1][S:39]([CH3:38])(=[O:41])=[O:40])=[CH:30][CH:29]=4)[N:8]=2)=[N:15][N:14]=[C:13]3[CH3:17])=[CH:27][CH:26]=1.[CH3:38][S:39]([N:1]([S:39]([CH3:38])(=[O:41])=[O:40])[C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:16]3[N:12]([CH:13]=[N:14][N:15]=3)[C:11]3[CH:18]=[CH:19][CH:20]=[CH:21][C:10]=3[C:9]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[N:8]2)=[CH:4][CH:3]=1)(=[O:41])=[O:40]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 18974883HCID 18974883, compound

Product 2

HCID 18974970HCID 18974970, compoundHCID 18975115HCID 18975115, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Aminobenzyl)-6-(4-chlorophenyl)-1-methyl-4H-2,3,4,5,10b-pentaazabenz[e]azulene (24.8 mg) obtained in Example 188 was dissolved in dichloromethane (2 ml) and triethylamine (30 μl) was added. The mixture was ice-cooled and methanesulfonyl chloride (7 μl) was added. The mixture was stirred under ice-cooling for 10 minutes and at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure and a 5% aqueous citric acid solution and ethyl acetate were added. The organic layer, was separated, and successively washed with a saturated aqueous sodium hydrogencarbonate solution and water. The organic layer was dried, filtered and concentrated under reduced pressure. The residue obtained was separated and purified by preparative thin-layer chromatography. Both compounds were individually crystallized from ethyl acetate-diethyl ether to give 8 mg of 6-(4-chlorophenyl)-4-(4-methylsulfonylaminobenzyl)-1-methyl-4H-2,3,4,5,10b-pentaazabenz[e]azulene (m.p. 273°-275° C.) and 16 mg of 4-[4-bis(methylsulfonyl)aminobenzyl]-6-(4-chlorophenyl)-4H-2,3,4,5,10b-pentaazabenz[e]azulene (m.p. 220°-221° C.).

Workup

  1. temperaturecooled
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additiona 5% aqueous citric acid solution and ethyl acetate were added
  4. customThe organic layer, was separated
  5. washsuccessively washed with a saturated aqueous sodium hydrogencarbonate solution and water
  6. customThe organic layer was dried
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue obtained
  10. customwas separated
  11. custompurified by preparative thin-layer chromatography
  12. customBoth compounds were individually crystallized from ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-471230156e4147249805e0ce31f7b931
Source dataset
uspto-grants-1998_09
Patent number
US05807850

Reaction notes

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