Ethylenediamine → HCID 178454516, compound

HRID 1056483Notes

Reaction equation

HRID 1056483 reaction equation
[C:1]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11](/[N:14]=[N:15]/[C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=O)=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)(=[O:5])[CH2:2][CH2:3][CH3:4].[CH2:26]([NH2:29])[CH2:27][NH2:28]>CO.O.C(Cl)(Cl)Cl>[NH2:28][CH2:27][CH2:26][NH:29][C:20](=[O:22])[C:19]1[CH:18]=[CH:17][C:16](/[N:15]=[N:14]/[C:11]2[CH:10]=[CH:9][C:8]([CH2:7][NH:6][C:1](=[O:5])[CH2:2][CH2:3][CH3:4])=[CH:13][CH:12]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 2

HCID 3301EthylenediamineHCID 178454517HCID 178454517, compound

Product 1

HCID 178454516HCID 178454516, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The solution of compound 10 (170 mg, 0.5 mmol) and ethylenediamine (601 mg, 10 mmol) in methanol (10 mL), water (5 mL) and chloroform (2.5 mL) was refluxed for 24 h. The solvents were evaporated, the residue dissolved in aqueous potassium hydroxide (15 mL, 1 M), and extracted with methylene chloride (4×15 mL). The combined organic phases were washed with water and brine, dried over magnesium sulfate, and the residue chromatographed on silica gel using chloroform—chloroform:methanol (10%) step-gradient as an eluent to give pure MPD021 (113 mg, 62%) as orange crystals. 1H NMR (400 MHz, DMSO-d6): δ 8.15 (d, J=8.4 Hz, 2H), 7.93-7.86 (m, 4H), 7.46 (d, J=8.4 Hz, 2H), 4.35 (s, 2H), 3.98 (t, J=6.0 Hz, 2H), 3.13 (t, J=6.0 Hz, 2H), 2.06 (t, J=7.2 Hz, 2H), 1.54-1.58 (m, 2H), 0.83 (t, J=7.2 Hz, 3H). 13C NMR (100.61 MHz, DMSO-d6): δ 174.22, 166.43, 155.51, 153.37, 139.21, 137.12, 127.14, 127.09, 122.89, 122.78, 61.11, 43.66, 42.69, 37.04, 19.14, 13.06. HRMS (m/z): [M+H]+ calcd. for C20H25N5O2 368.2081. found 368.2099.

Workup

  1. customThe solvents were evaporated
  2. dissolutionthe residue dissolved in aqueous potassium hydroxide (15 mL, 1 M)
  3. extractionextracted with methylene chloride (4×15 mL)
  4. washThe combined organic phases were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customthe residue chromatographed on silica gel
  7. custommethanol (10%) step-gradient as an eluent to give pure MPD021 (113 mg, 62%) as orange crystals

Sources & evidence

ORD record
ord-c02b2f0eb13c4b98b29cf49dbbeb8105
Source dataset
uspto-grants-2016_07
Patent number
US09399145B2

Reaction notes

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