Triethylamine → HCID 86629190, compound

HRID 1642054Notes

Reaction equation

HRID 1642054 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[N:12]3[CH:13]=[N:14][C:15]([C:16](O)=[O:17])=[C:11]3[CH2:10][N:9]=[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]=2[CH:25]=1)#[CH:2].[ClH:26].[CH2:27]([N:29]=C=NCCCN(C)C)[CH3:28].N1(O)C2C=CC=CC=2N=N1.C(N(CC)CC)C.Cl.C(N)C>CN(C=O)C>[ClH:26].[ClH:26].[CH2:27]([NH:29][C:16]([C:15]1[N:14]=[CH:13][N:12]2[C:6]3[CH:5]=[CH:4][C:3]([C:1]#[CH:2])=[CH:25][C:7]=3[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:9][CH2:10][C:11]=12)=[O:17])[CH3:28]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 11198Ethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21065274HCID 21065274, compound

Product 1

HCID 86629190HCID 86629190, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8-Ethynyl-6-phenyl-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylic acid (82 mg, 0.251 mmol) was dissolved in DMF (6 ml) and then N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (48 mg, 0.251 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (33.8 mg, 0.251 mmol), and triethylamine (70 μL, 0.501 mmol) were added. The solution was stirred for 15 min and then ethylamine hydrochloride (20.4 mg, 0.251 mmol) was added. The solution was stirred at room temperature for 3 days. The DMF was removed in vacuo. The residue was dissolved in ethyl acetate and extracted with water twice, then dried with brine. The ethyl acetate layer was then condensed with a stream of nitrogen, and dried in vacuo. The residue was dissolved in methylene chloride, and applied to a silica gel column. The product was eluted with ethyl acetate. The product fractions were concentrated in vacuo. The oily residue was dissolved in acetonitrile and several drops of concentrated HCl were added to give the HCl salt. The acetonitrile was removed in vacuo and the HCl salt was dried under high vacuum to give a yellow powder (75 mg, 77%).

Workup

  1. stirringThe solution was stirred at room temperature for 3 days
  2. customThe DMF was removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. extractionextracted with water twice
  5. dry with materialdried with brine
  6. customcondensed with a stream of nitrogen
  7. customdried in vacuo
  8. dissolutionThe residue was dissolved in methylene chloride
  9. washThe product was eluted with ethyl acetate
  10. concentrationThe product fractions were concentrated in vacuo
  11. dissolutionThe oily residue was dissolved in acetonitrile
  12. additionseveral drops of concentrated HCl were added

Sources & evidence

ORD record
ord-f045bc1c6ea54e8c87ca0498d331cf52
Source dataset
uspto-grants-2012_02
Patent number
US08119629B2

Reaction notes

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