Chloroform → 9,10-bis(N'-(3-(dimethylamino)propyl)-N-ethylcarbamimidoyloxyimino)-2,7-bis(azocan-1-ylsulfonyl)-9,10-dihydro-anthracene tetrahydrochloride

HRID 61972Notes

Reaction equation

HRID 61972 reaction equation
[N:1]1([S:9]([C:12]2[CH:25]=[CH:24][C:23]3[C:22](=[N:26][OH:27])[C:21]4[C:16](=[CH:17][C:18]([S:28]([N:31]5[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]5)(=[O:30])=[O:29])=[CH:19][CH:20]=4)[C:15](=[N:39][OH:40])[C:14]=3[CH:13]=2)(=[O:11])=[O:10])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:41][CH2:42][N:43]=[C:44]=[N:45][CH2:46][CH2:47][CH2:48][N:49]([CH3:51])[CH3:50].C(Cl)(Cl)[Cl:53]>>[ClH:53].[ClH:53].[ClH:53].[ClH:53].[CH3:50][N:49]([CH3:51])[CH2:48][CH2:47][CH2:46][N:45]=[C:44]([O:40][N:39]=[C:15]1[C:14]2[CH:13]=[C:12]([S:9]([N:1]3[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)(=[O:10])=[O:11])[CH:25]=[CH:24][C:23]=2[C:22](=[N:26][O:27][C:44](=[N:45][CH2:46][CH2:47][CH2:48][N:49]([CH3:51])[CH3:50])[NH:43][CH2:42][CH3:41])[C:21]2[C:16]1=[CH:17][C:18]([S:28]([N:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1)(=[O:29])=[O:30])=[CH:19][CH:20]=2)[NH:43][CH2:42][CH3:41]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178527264HCID 178527264, compound

Product 1

HCID 866421369,10-bis(N'-(3-(dimethylamino)propyl)-N-ethylcarbamimidoyloxyimino)-2,7-bis(azocan-1-ylsulfonyl)-9,10-dihydro-anthracene tetrahydrochlorideYield 68%

Procedure

Compound 2-22 (442 mg, 0.75 mmole), 4 mL of anhydrous chloroform and 400 mg of EDAC were stirred at 60° C. for 1 hr. The reaction mixture was condensed and chromatographed by HPLC. Combined fractions containing the desired product (MH+=899) were acidified by addition of 5 mL of 1N HCl and evaporated to dryness. The product was dissolved in distilled water and lyophilized to give 530 mg (68%) of white title compound.

Workup

  1. customcondensed
  2. customchromatographed by HPLC
  3. additionCombined fractions containing the desired product (MH+=899)
  4. additionwere acidified by addition of 5 mL of 1N HCl
  5. customevaporated to dryness
  6. dissolutionThe product was dissolved in distilled water

Sources & evidence

ORD record
ord-c95930bde6634d578f00f2101914cb9a
Source dataset
uspto-grants-2016_09
Patent number
US09446021B2

Reaction notes

Loading…