Ethylenediamine → HCID 58747061, compound

HRID 724533Notes

Reaction equation

HRID 724533 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[CH:7]=[CH:8][C:9]2[O:13][C:12]([C:14]([NH:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[NH:22][C:21]([C:26]([OH:28])=O)=[CH:20]4)=[O:15])=[CH:11][C:10]=2[CH:29]=1)=[O:4].[CH2:30]([NH2:33])[CH2:31][NH2:32]>>[NH2:32][CH2:31][CH2:30][NH:33][C:26]([C:21]1[NH:22][C:23]2[C:19]([CH:20]=1)=[CH:18][C:17]([NH:16][C:14]([C:12]1[O:13][C:9]3[CH:8]=[CH:7][C:6]([NH:5][C:3](=[O:4])[CH2:2][NH2:1])=[CH:29][C:10]=3[CH:11]=1)=[O:15])=[CH:25][CH:24]=2)=[O:28]

Participants

3

Reactant 2

HCID 3301EthylenediamineHCID 21880768HCID 21880768, compound

Product 1

HCID 58747061HCID 58747061, compound

Procedure

To 340 mg (0.05 mmol) 131 resin 8 mL 1,2-ethylenediamine was added. The resin was agitated for 1 hr at ambient temperature then it was filtered off, washed twice with DMF. The filtrates were pooled and were evaporated to dryness. The remaining oily residue was dissolved in DMF and evaporated again in order to get rid of the amine traces. The crude material was dissolved in 5 mL aqueous 0.1% TFA solution and was purified on a preparative reverse phase HPLC column using acetonitrile gradient. The fractions containing the pure product were pooled, evaporated to dryness dissolved in 3 mL methanol and treated with 1 mL 4.0M HCl in dioxane. 133 was precipitated with ether as bis-HCl salt, filtered off and dried to yield 44.8 mg (88%). MS: 435.19 (M+H+).

Workup

  1. filtrationit was filtered off
  2. washwashed twice with DMF
  3. customwere evaporated to dryness
  4. dissolutionThe remaining oily residue was dissolved in DMF
  5. customevaporated again in order

Sources & evidence

ORD record
ord-7bf99a618a3e4990921cc3192cae99c5
Source dataset
uspto-grants-2006_11
Patent number
US07141680B2

Reaction notes

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