Triethylamine → HCID 54290741, compound

HRID 580851Notes

Reaction equation

HRID 580851 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]3[CH:14]([CH2:15][CH2:16][C:17]([OH:19])=O)[CH2:13][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>[NH3:1].[CH2:20]([N:27]1[CH2:32][CH2:31][N:30]([NH:34][C:17](=[O:19])[CH2:16][CH2:15][CH: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][CH2:13]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 67581628HCID 67581628, compound

Product 2

HCID 222AmmoniaHCID 54290741HCID 54290741, compoundYield 139.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(5-(1,2,4-triazol-1-yl)-2,3-dihydro-1H-pyrrolo[2,3-c]pyridin-3-yl)propionic acid (0.108 g) in dry DMF (3 mL) was added 1-benzylpiperazine (0.11 mL, 0.63 mmol), 1-hydroxybenzotriazole (71 mg, 0.52 mmol), 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide hydrochloride (0.1 g, 0.52 mmol) and triethylamine (73 μL, 0.52 mmol) and this mixture was stirred at ambient temperature under nitrogen for 64 hours. The solvent was evaporated in vacuo and the residue was partitioned between ethyl acetate (25 mL) and water (25 mL). The two phases were separated and the aqueous phase was extracted with ethyl acetate (2×20 mL). The combined organics were dried (Na2SO4) and evaporated in vacuo. The residue was chromatographed on silica eluting with a gradient of 2 to 5% MeOH in DCM, followed by 95:5:1, DCM:MeOH:NH3 to give the title compound (0.126 g, 72%) as a pale yellow foam. 1H NMR (360 MHz, CDCl3) δ 1.88-1.96 (1H, m), 2.07-2.15 (1H, m), 2.30-2.40 (6H, m), 3.28-3.60 (8H, m), 3.72-3.83 (2H, m), 7.19-7.27 (5H, m), 7.57 (1H, s), 7.66 (1H, s), 7.95 (1H, s) and 8.91 (1H, s).

Workup

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

Sources & evidence

ORD record
ord-6a32a66873854f6c8b50e290a47b272a
Source dataset
uspto-grants-1999_07
Patent number
US05919783

Reaction notes

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