Triethylamine → HCID 178491159, compound

HRID 1934675Notes

Reaction equation

HRID 1934675 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].C(N(CC)CC)C.[NH2:13][C@H:14]1[CH2:19][CH2:18][C@H:17]([NH:20][C:21]2[CH:40]=[CH:39][C:38]([N+:41]([O-:43])=[O:42])=[CH:37][C:22]=2[C:23]([NH:25][CH2:26][C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[C:29]([O:35][CH3:36])[CH:28]=2)=[O:24])[CH2:16][CH2:15]1>C(Cl)(Cl)Cl>[CH3:36][O:35][C:29]1[CH:28]=[C:27]([CH:32]=[CH:31][C:30]=1[O:33][CH3:34])[CH2:26][NH:25][C:23](=[O:24])[C:22]1[CH:37]=[C:38]([N+:41]([O-:43])=[O:42])[CH:39]=[CH:40][C:21]=1[NH:20][C@H:17]1[CH2:16][CH2:15][C@H:14]([NH:13][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 178491154HCID 178491154, compound

Product 1

HCID 178491159HCID 178491159, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methanesulfonyl chloride (54 mg) and triethylamine (48 mg) were added to a solution of 2-(trans-4-aminocyclohexylamino)-N-(3,4-dimethoxybenzyl)-5-nitrobenzamide (134 mg) in chloroform (2 mL). The mixture was stirred for an hour at ambient temperature. Methanesulfonyl chloride (54 mg) and triethylamine (48 mg) were added to the reaction mixture. After stirring for an hour at ambient temperature, the mixture was concentrated in vacuo. The residue was partitioned between ethyl acetate and 3.6% hydrochloric acid. The separated organic layer was washed with an saturated aqueous sodium bicarbonate solution and brine, dried over magnesium sulfate and concentrated in vacuo. The residual crystals were suspended in hot ethanol and cooled with stirring. The resultant was collected by filtration and washed with ethanol to give N-(3,4-dimethoxybenzyl)-2-[trans-4-(methanesulfonylamino)cyclohexylamino]-5-nitrobenzamide (142 mg) as yellow crystals.

Workup

  1. stirringAfter stirring for an hour at ambient temperature
  2. concentrationthe mixture was concentrated in vacuo
  3. customThe residue was partitioned between ethyl acetate and 3.6% hydrochloric acid
  4. washThe separated organic layer was washed with an saturated aqueous sodium bicarbonate solution and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. temperaturecooled
  8. stirringwith stirring
  9. filtrationThe resultant was collected by filtration
  10. washwashed with ethanol

Sources & evidence

ORD record
ord-3e225763b6e34940957009c56ffabb12
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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