4-Methylmorpholine → HCID 66824539, compound

HRID 1468624Notes

Reaction equation

HRID 1468624 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH3:23])[C:7](=[O:22])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)=[C:4]([NH:24][NH2:25])[N:3]=1.C1C=CC2N([OH:35])N=NC=2C=1.CN1[CH2:42][CH2:41][O:40]CC1.CCN=C=N[CH2:48][CH2:49][CH2:50]N(C)C.Cl>CN(C)C=O.O>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]([CH3:23])[C:7](=[O:22])[N:8]2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)=[C:4]([NH:24][NH:25][C:41]([C:42]2[O:35][CH:50]=[CH:49][CH:48]=2)=[O:40])[N:3]=1

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66824447HCID 66824447, compound

Product 1

HCID 66824539HCID 66824539, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
26 °C

Procedure

2-amino-9-[(3,4-dimethoxyphenyl)methyl]-6-hydrazino-7-methyl-purin-8-one (4.6 g, 13.38 mmol) obtained in step 4,2-furoic acid (1.5 g, 13.38 mmol), HOBT (1.8 g, 13.38 mmol) and N-methylmorpholine (2.20 ml, 20.07 mmol) were taken in dimethylformamide (15 ml). EDC.HCl (3.8 g, 20.07 mmol) was added to the reaction mixture and stirred at 25-27° C. for 3 hours. Reaction mixture was cooled to 0° C. Water was added and solid obtained was filtered off, washed with cold water, n-hexane and dried to obtain N′-[2-amino-9-[(3,4-dimethoxyphenyl)methyl]-7-methyl-8-oxo-purin-6-yl]furan-2-carbohydrazide (5.5 g, 95) as an off white solid.

Workup

  1. customReaction mixture
  2. temperaturewas cooled to 0° C
  3. customsolid obtained
  4. filtrationwas filtered off
  5. washwashed with cold water, n-hexane
  6. customdried

Sources & evidence

ORD record
ord-633a616ce8404540b766a7f14d381726
Source dataset
uspto-grants-2015_04
Patent number
US09006177B2

Reaction notes

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