Triethylamine → HCID 70042540, compound

HRID 464633Notes

Reaction equation

HRID 464633 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[N:8]=[N:7][C:6]([CH2:9][O:10][CH2:11][C:12]2[NH:13][C:14]([CH3:35])=[C:15]([C:31]([O:33][CH3:34])=[O:32])[CH:16]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[C:24]=3[Cl:30])[C:17]=2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[N:5]1.C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>ClCCl>[Cl:30][C:24]1[C:25]([Cl:29])=[CH:26][CH:27]=[CH:28][C:23]=1[CH:16]1[C:15]([C:31]([O:33][CH3:34])=[O:32])=[C:14]([CH3:35])[NH:13][C:12]([CH2:11][O:10][CH2:9][C:6]2[N:7]=[N:8][N:4]([CH2:3][CH2:2][NH:1][S:44]([CH3:43])(=[O:46])=[O:45])[N:5]=2)=[C:17]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70042414HCID 70042414, compound

Product 1

HCID 70042540HCID 70042540, compoundYield 29.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(2-aminoethyl)-5-{[4-(2,3-dichlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridin-2-yl]methoxymethyl}tetrazole (0.33 g), triethylamine (65 mg) and methanesulphonyl chloride (71 mg) in dichloromethane (15 ml) was heated under reflux for 2 hours and then evaporated. The residue was purified by chromatography on silica (6 g) using dichloromethane plus from 0 to 1% by volume of methanol as eluant. Appropriate fractions were combined and evaporated. The residual solid was recrystallized from ethyl acetate and dried to give the title compound (111 mg) as a hydrate, m.p. 245°-247° C. Found: C,46.23; H,5.02; N,13.82. C23H28Cl2N6O7S.H2O requires: C,46.26; H,5.19; N,14.08%.

Workup

  1. temperatureunder reflux for 2 hours
  2. customevaporated
  3. customThe residue was purified by chromatography on silica (6 g)
  4. customevaporated
  5. customThe residual solid was recrystallized from ethyl acetate
  6. customdried

Sources & evidence

ORD record
ord-cfa9086281e042909dc89968bcbf7f17
Source dataset
uspto-grants-1985_10
Patent number
US04548935

Reaction notes

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