Ethylenediamine → HCID 178439077, compound

HRID 1056481Notes

Reaction equation

HRID 1056481 reaction equation
[OH:1][C:2]1[C:7]([CH:8]([CH3:10])[CH3:9])=[CH:6][C:5]([CH2:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21](/[N:24]=[N:25]/[C:26]3[CH:35]=[CH:34][C:29]([C:30]([O:32]C)=O)=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)=[O:15])=[CH:4][C:3]=1[CH:36]([CH3:38])[CH3:37].[CH2:39]([NH2:42])[CH2:40][NH2:41]>CO.O.C(Cl)(Cl)Cl>[NH2:41][CH2:40][CH2:39][NH:42][C:30](=[O:32])[C:29]1[CH:28]=[CH:27][C:26](/[N:25]=[N:24]/[C:21]2[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:5]3[CH:6]=[C:7]([CH:8]([CH3:9])[CH3:10])[C:2]([OH:1])=[C:3]([CH:36]([CH3:38])[CH3:37])[CH:4]=3)=[CH:19][CH:20]=2)=[CH:35][CH:34]=1

Participants

6

Reactant 2

HCID 3301EthylenediamineHCID 178498196HCID 178498196, compound

Product 1

HCID 178439077HCID 178439077, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

The solution of the compound 9 (258 mg, 0.50 mmol) and ethylenediamine (600 mg, 10 mmol) in methanol (10 mL), water (5 mL) and chloroform (2.5 mL) was refluxed for 24 h. The solvents were then evaporated, the residue was dissolved in 1N potassium hydroxide (15 mL), and the mixture extracted with methylene chloride (4×15 mL). The combined organic phases were washed with water and brine, dried over magnesium sulfate, concentrated under vacuum, and the residue chromatographed on silica gel using chloroform and chloroform-methanol (5%) step-gradient as an eluent to produce pure MCP088 (201 mg, 74%) as orange crystals. 1H NMR (360 MHz, CD3OD): δ 8.04-7.91 (m, 6H), 7.50 (d, J=8.4 Hz, 2H), 6.83 (s, 2H), 4.47 (s, 2H), 3.49 (t, J=6.4 Hz, 2H), 3.26 (septet, J=6.8 Hz, 2H), 2.90 (t, J=6.4 Hz, 2H), 2.55 (t, J=7.6 Hz, 2H), 2.30 (t, J=7.4 Hz, 2H), 1.92 (q, J=7.4 Hz, 2H), 1.19 (d, J=6.8 Hz, 12H). 13C NMR (90.55 MHz, CD3OD): δ 175.13, 168.66, 154.57, 152.02, 148.72, 143.39, 136.55, 135.84, 133.40, 128.42, 128.38, 128.20, 129.90, 123.21, 122.99, 122.65, 120.98, 120.02, 42.66, 42.48, 40.89, 35.54, 35.08, 28.21, 26.83, 22.48. HRMS (m/z): [M+H]+ calcd. for C32H41N5O3 544.3282. found 544.3308.

Workup

  1. customThe solvents were then evaporated
  2. dissolutionthe residue was dissolved in 1N potassium hydroxide (15 mL)
  3. extractionthe mixture extracted 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. concentrationconcentrated under vacuum
  7. customthe residue chromatographed on silica gel
  8. customto produce pure MCP088 (201 mg, 74%) as orange crystals

Sources & evidence

ORD record
ord-727bf87fa62b4cf29908bb602569efec
Source dataset
uspto-grants-2016_07
Patent number
US09399145B2

Reaction notes

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