Triethylamine → HCID 86753095, compound

HRID 2393439Notes

Reaction equation

HRID 2393439 reaction equation
[N:1]1([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]=[N:4][CH:3]=[N:2]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>[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:1]4[CH:5]=[N:4][CH:3]=[N:2]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

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 759941-BenzylpiperazineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57310684HCID 57310684, compound

Product 1

HCID 86753095HCID 86753095, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl)propionic acid (0.65 g) in dry DMF (5 mL) was added 1-benzylpiperazine (0.36 mL, 2.3 mmol), 1-hydroxybenzotriazole (0.255 g, 1.9 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (0.362 g, 1.9 mmol) and triethylamine (0.26 mL, 1.9 mmol) and this mixture was stirred at ambient temperature under nitrogen for 16 hours. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (25 mL) and water (25 mL) and Na2CO3 (sat., 1 mL). The two phases were separated and the aqueous phase was extracted with ethyl acetate (3×25 mL). The combined organics were dried (Na2 SO4) and evaporated in vacuo. The residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM to give the title compound (0.625 g, 100%) as a pale yellow foam. 1H NMR (360 MHz, CDCl3) δ 2.28-2.46 (4H, m), 2.70 (2H, t, J=7.1Hz), 3.15 (2H, t, J=7.2Hz), 3.37-3.43 (2H, m), 3.50 (2H, s), 3.60-3.68 (2H, m), 7.23-7.34 (6H, m), 8.05 (1H, s), 8.10 (1H, s), 8.58 (1H, s), 8.69 (1H, br s) and 9.14 (1H, s).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe residue was partitioned between ethyl acetate (25 mL) and water (25 mL) and Na2CO3 (sat., 1 mL)
  3. customThe two phases were separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (3×25 mL)
  5. customThe combined organics were dried (Na2 SO4)
  6. customevaporated in vacuo
  7. customThe residue was chromatographed on silica eluting with a gradient of 5 to 10% MeOH in DCM

Sources & evidence

ORD record
ord-f014b17226334c80941f4cc7cc79225e
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

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