Triethylamine → HCID 86753096, compound

HRID 2393451Notes

Reaction equation

HRID 2393451 reaction equation
[N:1]1[N:2]=[CH:3][N:4]([C:6]2[CH:7]=[C:8]3[C:14]([CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:13][NH:12][C:9]3=[CH:10][N:11]=2)[CH:5]=1.[CH2:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O[N:34]1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(CC)CC)C>CN(C=O)C>[NH3:1].[CH2:20]([N:27]1[CH2:32][CH2:31][N:30]([NH:34][C:17](=[O:19])[CH2:16][CH2:15][C:14]2[C:8]3[C:9](=[CH:10][N:11]=[C:6]([N:4]4[CH:5]=[N:1][N:2]=[CH:3]4)[CH:7]=3)[NH:12][CH:13]=2)[CH2:29][CH2:28]1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18975307HCID 18975307, compound

Product 2

HCID 222AmmoniaHCID 86753096HCID 86753096, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(5-(1,2,4-triazol-4-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)propionic acid (0.23 g) in dry DMF (3 mL) was added 1-benzylpiperazine (0.1 mL, 0.58 mmol), 1-hydroxybenzotriazole (66 mg, 0.49 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (93 mg, 0.49 mmol) and triethylamine (68 μL, 0.4 mmol) and this mixture was stirred at ambient temperature under nitrogen for 24 hours. The solvent was evaporated in vacuo and the residue partitioned between ethyl acetate (25 mL) and water (20 mL). The two phases were separated and the aqueous phase was extracted with ethyl acetate (3×25 mL). The combined organics were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica eluting with 90:10:1, DCM:MeOH:NH3 to give the title compound (30 mg, 19%) as a colourless solid. mp 185° C. (dec.). 1H NMR (360 MHz, CDCl3 :d4 -MeOH 9:1) δ 2.29-2.34 (2H, m), 2.35-2.42 (2H, m), 2.70 (2H, t, J=7.4Hz), 3.12 (2H, t, J=7.4Hz), 3.36-3.43 (2H, m), 3.48 (2H, s), 3.58-3.64 (2H, m), 7.24-7.35 (5H, m), 7.37 (1H, s), 7.67 (1H, s), 8.60 (1H, s) and 8.93 (2H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue partitioned between ethyl acetate (25 mL) and water (20 mL)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×25 mL)
  5. dry with materialThe combined organics were dried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica eluting with 90:10:1, DCM

Sources & evidence

ORD record
ord-091302ab33b849f1be320de000b1f96f
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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