Pyridine → HCID 67335586, compound

HRID 1675226Notes

Reaction equation

HRID 1675226 reaction equation
N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.[C:19]([OH:23])(=O)[CH:20]=[CH2:21].[NH2:24][CH2:25][CH2:26][C:27]([NH:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[N:36]=[CH:35][N:34]=[C:33]2[NH:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH2:48][C:49]2[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=2)=[C:43]([Cl:55])[CH:42]=1)=[O:28]>C1COCC1>[Cl:55][C:43]1[CH:42]=[C:41]([NH:40][C:33]2[C:32]3[C:37](=[CH:38][CH:39]=[C:30]([NH:29][C:27]([CH2:26][CH2:25][NH:24][C:19](=[O:23])[CH:20]=[CH2:21])=[O:28])[CH:31]=3)[N:36]=[CH:35][N:34]=2)[CH:46]=[CH:45][C:44]=1[O:47][CH2:48][C:49]1[CH:50]=[N:51][CH:52]=[CH:53][CH:54]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6581Acrylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67334602HCID 67334602, compound

Product 1

HCID 67335586HCID 67335586, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

46 μl of pyridine and 85 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added to 31 μl of acrylic acid dissolved in 3 ml of THF at 0° C., reacted with 100 mg of the compound (132-1) of Example 132 for 30 mins, and stirred for 2 hours while heating to room temperature. The reacted solution was extracted with 6 ml of ethylacetate 3 times after adding 4 ml of water, dried over anhydrous magnesium sulfate, filtered and distilled under a reduced pressure, and the resulting residue was subjected to column chromatography (eluent-chloroform:methanol=15:1) to obtain the title compound (20 mg, 18%).

Workup

  1. extractionThe reacted solution was extracted with 6 ml of ethylacetate 3 times
  2. additionafter adding 4 ml of water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. distillationdistilled under a reduced pressure

Sources & evidence

ORD record
ord-60045dc3b400431095c05ffca3485e2b
Source dataset
uspto-grants-2011_08
Patent number
US08003658B2

Reaction notes

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