1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 67135025, compound

HRID 536037Notes

Reaction equation

HRID 536037 reaction equation
[NH2:1][C:2]1[C:3](=[O:13])[N:4]([CH2:10][CH2:11][CH3:12])[C:5](=[O:9])[NH:6][C:7]=1[NH2:8].[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[N:22]1[C:26](=[O:27])[CH2:25][CH:24]([CH2:28][N:29]2[CH:33]=[C:32]([C:34](O)=[O:35])[CH:31]=[N:30]2)[CH2:23]1.CCN=C=NCCCN(C)C.Cl>CO>[NH2:8][C:7]1[NH:6][C:5](=[O:9])[N:4]([CH2:10][CH2:11][CH3:12])[C:3](=[O:13])[C:2]=1[NH:1][C:34]([C:32]1[CH:31]=[N:30][N:29]([CH2:28][CH:24]2[CH2:25][C:26](=[O:27])[N:22]([C:16]3[CH:17]=[CH:18][C:19]([F:21])=[CH:20][C:15]=3[F:14])[CH2:23]2)[CH:33]=1)=[O:35]

Participants

5

Reactant 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 109542025,6-Diamino-3-propylpyrimidine-2,4(1H,3H)-dioneHCID 67135277HCID 67135277, compound

Product 1

HCID 67135025HCID 67135025, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5,6-Diamino-3-propyl-1H-pyrimidine-2,4-dione (0.12 g, 0.67 mmol) and 1-[1-(2,4-Difluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid (0.18 g, 0.56 mmol) in methanol (6 ml) was cooled to 0° C. and added EDCI.HCl (0.15 g, 0.78 mmol) and stirred at 25° C. for 20 hours. Solvents were removed under reduced pressure and to this reaction mixture water (10 ml) was added. Solid obtained was filtered off and washed with cold water (20 ml) followed by diethyl ether (25 ml). It was then dried and the crude product was purified by column chromatography using silica gel (100-200 mesh) and 6% methanol in DCM as an eluent to obtain 1-[1-(2,4-Difluoro-phenyl)-5-oxo-pyrrolidin-3-ylmethyl]-1H-pyrazole-4-carboxylic acid (6-amino-2,4-dioxo-3-propyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide (0.165 g, 60%) as an off white solid.

Workup

  1. customSolvents were removed under reduced pressure and to this reaction mixture water (10 ml)
  2. additionwas added
  3. customSolid obtained
  4. filtrationwas filtered off
  5. washwashed with cold water (20 ml)
  6. customIt was then dried
  7. customthe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-8dfd1a535b6947e38d1e6dab62253f40
Source dataset
uspto-grants-2014_10
Patent number
US08859566B2

Reaction notes

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