4-Methylmorpholine → 2-(1-hydroxyethyl)-N-{1-[3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

HRID 1368299Notes

Reaction equation

HRID 1368299 reaction equation
[OH:1][CH:2]([CH:4]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([OH:7])=O)[CH3:3].ON1C2C=CC=C[C:21]=2N=N1.CN1CCOCC1.Cl.CN(C)CCCN=C=NCC.[NH2:46][CH:47]([C:49]1[C:50](=[O:64])[NH:51][C:52]([CH2:55][C:56]2[CH:61]=[CH:60][C:59](OC)=[CH:58][CH:57]=2)=[N:53][N:54]=1)[CH3:48]>>[OH:1][CH:2]([CH:4]([CH2:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([NH:46][CH:47]([C:49]1[C:50](=[O:64])[NH:51][C:52]([CH2:55][C:56]2[CH:61]=[CH:60][C:59]([CH3:21])=[CH:58][CH:57]=2)=[N:53][N:54]=1)[CH3:48])=[O:7])[CH3:3]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 183340382-(1-Hydroxyethyl)-5-phenylpentanoic acidHCID 1356979216-(1-aminoethyl)-3-(4-methoxybenzyl)-1,2,4-triazin-5(4H)-one

Product 1

HCID 1358247302-(1-hydroxyethyl)-N-{1-[3-(4-methylbenzyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}-5-phenylpentanamide

Conditions

Temperature
-20 °C

Procedure

1.09 g (4.91 mmol) of 2-(1-hydroxyethyl)-5-phenylpentanoic acid are treated with 660 mg (4.61 mmol) of 1-hydroxy-1H-benzotriazole and 990 mg (9.82 mmol) of 4-methylmorpholine and the mixture is cooled to −20° C. After addition of 940 mg (4.61 mmol) of N′-(3-dimethylaminopropyl)-N-ethylcarbodiimide hydrochloride, the mixture is stirred for 30 min. At the same time, the cooling bath is removed. Then, after again cooling to −20° C., 1.00 g (4.09 mmol) of 6-(1-aminoethyl)-3-(4-methoxybenzyl)-1,2,4-triazin-5(4H)-one is added and the mixture is stirred overnight while warming to room temperature. For work-up, the dichloromethane phase is washed with 1N potassium hydrogensulphate solution and then with saturated sodium hydrogencarbonate solution. The dried organic phase is concentrated and chromatographed using the eluent dichloromethane/methanol 100/1 to 30/1.

Workup

  1. customAt the same time, the cooling bath is removed
  2. temperatureThen, after again cooling to −20° C.
  3. stirringthe mixture is stirred overnight
  4. temperaturewhile warming to room temperature
  5. washFor work-up, the dichloromethane phase is washed with 1N potassium hydrogensulphate solution
  6. concentrationThe dried organic phase is concentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-c4592f1bf72243a2a9a34ab591bdcb15
Source dataset
uspto-grants-2003_06
Patent number
US06573263B2

Reaction notes

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