Triethylamine → HCID 86753097, compound

HRID 2393452Notes

Reaction equation

HRID 2393452 reaction equation
C(N1CCN([NH:14][C:15](=[O:32])[CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][N:23]=[C:24]([N:27]4[CH:31]=[N:30][CH:29]=[N:28]4)[CH:25]=3)[NH:20][CH:19]=2)CC1)C1C=CC=CC=1.[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.C(N(CC)CC)C>CN(C=O)C>[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][N:43]([NH:14][C:15](=[O:32])[CH2:16][CH2:17][C:18]2[C:26]3[C:21](=[CH:22][N:23]=[C:24]([N:27]4[CH:31]=[N:30][CH:29]=[N:28]4)[CH:25]=3)[NH:20][CH:19]=2)[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:34])[CH3:35]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86753095HCID 86753095, compound

Product 1

HCID 86753097HCID 86753097, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-(1,2,4-triazol-1-yl)-1H-pyrrolo[2,3-c]pyridin-3-yl) propionic acid (0.34 g, 1.3 mmol) (prepared as described in Example 53 Step 7) in anhydrous DMF (5 ml) was added 1-tert-butyloxycarbonylpiperazine (0.5 g, 2.7 mmol), 1-hydroxybenzotriazole (225 mg, 1.7 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.45 g, 2.3 mmol) and triethylamine (0.23 ml, 1.7 mmol). The mixture was stirred at room temperature for 2 days. The solvent was evaporated and the residue partitioned between ethyl acetate (25 ml) and water (20 ml). The organic layer was separated and the aqueous phase extracted with ethyl acetate (3×20 ml). The combined organic layers were dried (Na2 SO4) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2 /MeOH (90:10) to afford the title compound, with some impurities, as a pale yellow foam.

Workup

  1. customThe solvent was evaporated
  2. customthe residue partitioned between ethyl acetate (25 ml) and water (20 ml)
  3. customThe organic layer was separated
  4. extractionthe aqueous phase extracted with ethyl acetate (3×20 ml)
  5. customThe combined organic layers were dried (Na2 SO4)
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with CH2Cl2 /MeOH (90:10)

Sources & evidence

ORD record
ord-0ebec9563b2e4609bbec4e1633c68eac
Source dataset
uspto-grants-1998_09
Patent number
US05807857

Reaction notes

Loading…