Water → HCID 54387522, compound

HRID 1781169Notes

Reaction equation

HRID 1781169 reaction equation
[CH2:1](N)[CH2:2][CH3:3].CCN=C=N[CH2:10][CH2:11][CH2:12][N:13]([CH3:15])C.Cl.[CH:17]1[CH:18]=[CH:19][C:20]2N(O)N=N[C:21]=2[CH:22]=1.CCN([CH2:32][CH3:33])CC.[OH2:34]>C1COCC1>[C:21]1([CH2:1][CH2:2][CH2:3][C@@H:11]([CH3:10])[C:12]([NH:13][CH2:15][CH2:32][CH3:33])=[O:34])[CH:20]=[CH:19][CH:18]=[CH:17][CH:22]=1

Participants

7

Reactant 5

HCID 962WaterHCID 7852PropylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 54387522HCID 54387522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the compound resulting from Example 82A (0.12 g, 0.63 mmol), n-propylamine (0.052 mL, 0.63 mmol), EDCl (0.14 g, 0.73 mmol), HOBT (0.02 g, 1.4 mmol), Et3N (0.10 mL, 0.73 mmol), and 3.5 mL anydrous THF was stirred at room temperature for 24 hours. Water was added, and the mixture was extracted with EtOAc (3×). The combined organic layers were washed with 5% sodium bicarbonate, H2O, 1N HCl and saturated NaCl solution, dried (MgSO4), filtered, and concentrated in vacuo to afford the title compound (0.13 g) as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 0.90 (t, 3H), 1.12 (d, 3H), 1.38-1.58 (m, 3H), 1.59-1.78 (m, 3H), 2.15 (m, 1H), 2.60 (m, 2H), 3.20 (q, 2H), 5.35 (brs, 1H) 7.20 (t, 3H), 7.28 (m,2H). MS (DCl/NH3) m/e 234 (M+H)+.

Workup

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. washThe combined organic layers were washed with 5% sodium bicarbonate, H2O, 1N HCl and saturated NaCl solution
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b0ce23bdeb74629ad420da9020a3807
Source dataset
uspto-grants-1997_05
Patent number
US05631401

Reaction notes

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