4-Methylmorpholine → Ethyl[3-(3-{4-[(2-acetylaminoacetylamino)methyl]phenyl}-6-oxo-6h-pyridazin-1-ylmethyl)phenyl]carbamate

HRID 383637Notes

Reaction equation

HRID 383637 reaction equation
[C:1]([NH:4][CH2:5][C:6]([OH:8])=O)(=[O:3])[CH3:2].CN1CCOCC1.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.[CH2:38]([O:40][C:41](=[O:65])[NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49][N:50]2[C:55](=[O:56])[CH:54]=[CH:53][C:52]([C:57]3[CH:62]=[CH:61][C:60]([CH2:63][NH2:64])=[CH:59][CH:58]=3)=[N:51]2)[CH:44]=1)[CH3:39]>CN(C=O)C>[CH2:38]([O:40][C:41](=[O:65])[NH:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([CH2:49][N:50]2[C:55](=[O:56])[CH:54]=[CH:53][C:52]([C:57]3[CH:58]=[CH:59][C:60]([CH2:63][NH:64][C:6](=[O:8])[CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[CH:61][CH:62]=3)=[N:51]2)[CH:44]=1)[CH3:39]

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 10972AcetylglycineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59406699Ethyl{3-[3-(4-aminomethylphenyl)-6-oxo-6h-pyridazin-1-ylmethyl]phenyl}carbamate

Product 1

HCID 25118490Ethyl[3-(3-{4-[(2-acetylaminoacetylamino)methyl]phenyl}-6-oxo-6h-pyridazin-1-ylmethyl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

61 mg (0.52 mmol) of N-acetylglycine are suspended in 2 ml of DMF, 106 μl (0.95 mmol) of 4-methylmorpholine, 66 mg (0.47 mmol) of 1-hydroxybenzotriazole and 184 mg (0.95 mmol) of N-(3-dimethylamino-propyl)-N′-ethylcarbodiimide hydrochloride are added. The reaction mixture is stirred at room temperature for 10 min, 180 mg (0.48 mmol) of ethyl{3-[3-(4-aminomethylphenyl)-6-oxo-6H-pyridazin-1-ylmethyl]-phenyl}carbamate are subsequently added, and the mixture is stirred at room temperature for 24 h.

Workup

  1. stirringthe mixture is stirred at room temperature for 24 h.

Sources & evidence

ORD record
ord-956ff54e833c41dd962f219daf89fbf4
Source dataset
uspto-grants-2013_02
Patent number
US08367668B2

Reaction notes

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