Hydrochloric Acid → HCID 131728149, compound

HRID 12999Notes

Reaction equation

HRID 12999 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]([CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:27])[CH3:26])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[ClH:30]>C(O)C>[ClH:30].[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][N:16]([CH2:28][CH3:29])[CH2:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:27])[CH3:26])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24744195n-{3-[3-(Anthracen-9-ylmethyl-ethyl-amino)-propylamino]-propyl}-acetamide

Product 1

HCID 131728149HCID 131728149, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of compound 23 (100 mg, 0.26 mmole) was dissolved in absolute ethanol (13 mL) and stirred at 0° C. for 10 minutes. A 4N HCl solution (22 mL) was added to the reaction mixture dropwise and stirred at 0° C. for 20 minutes and then at room temperature overnight. The solution was concentrated in vacuo to give 24 as a yellow solid in 96% yield. 1H NMR (D2O) δ 8.59 (s, 1H), 8.10 (m, 4H), 7.70 (m, 2H), 7.61 (m, 2H), 5.13 (s, 2H), 3.41 (br m, 2H), 3.12 (br m, 4H), 2.79 (br m, 4H), 1.98 (s, 3H), 1.71 (q, 2H), 1.43 (m, 5H); 13C NMR (D2O): δ 174.5, 131.3, 130.8, 129.8, 128.2, 125.7, 122.5, 119.1, 50.0, 49.7, 49.4, 44.9, 44.1, 36.0, 25.5, 21.9, 20.8, 8.7. HRMS (FAB) calcd for C25H33N3O.2HCl (M+H−2HCl)+ 392.2701, Found 392.2702.

Workup

  1. stirringstirred at 0° C. for 20 minutes
  2. customat room temperature
  3. customovernight
  4. concentrationThe solution was concentrated in vacuo

Sources & evidence

ORD record
ord-2ab243b252d449b08a2da1edce534b32
Source dataset
uspto-grants-2010_06
Patent number
US07728041B2

Reaction notes

Loading…