Triethylamine → HCID 9891351, compound

HRID 1602356Notes

Reaction equation

HRID 1602356 reaction equation
[C:1]([C:3]1[CH:26]=[CH:25][C:6]([CH2:7][N:8]2[C:12]([CH2:13][NH:14][CH2:15][CH2:16][NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].C(N(CC)CC)C.[CH3:34][C:35](OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=[O:36].CCOC(C)=O>C(Cl)Cl>[ClH:24].[ClH:24].[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:12]([CH2:13][N:14]([CH2:15][CH2:16][NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=3)[C:35](=[O:36])[CH3:34])=[CH:11][N:10]=[CH:9]2)=[CH:25][CH:26]=1)#[N:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterHCID 19611597HCID 19611597, compound

Product 1

HCID 9891351HCID 9891351, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of the diamine 8 (150 mg) in 2.5 mL of CH2Cl2 was added triethylamine (0.057 mL). The solution was cooled to 0° C., and acetic anyhydride (0.019 mL) was added. The reaction was stirred overnight, allowing it to gradually warm to room temperature. The mixture was poured into EtOAc and washed with sat. aq. NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated in vacuo. This material was purified by silica gel chromatography (2.5-5% MeOH/CH2Cl2), taken up in CH2Cl2 and treated with 1 M HCl/ether solution, and concentrated in vacuo. The product hydrochloride 1 was isolated as a white solid.

Workup

  1. temperatureto gradually warm to room temperature
  2. washwashed with sat. aq. NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis material was purified by silica gel chromatography (2.5-5% MeOH/CH2Cl2)
  7. additiontreated with 1 M HCl/ether solution
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-95ae5b4ab80f4b0b9587a5c2d47921b3
Source dataset
uspto-grants-1999_11
Patent number
US05981562

Reaction notes

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