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Pyridine → HCID 136352208, compound

HRID 1631657
Notes
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Reaction equation

HRID 1631657 reaction equation
N1C=CC=CC=1.Cl.CN(C)CCCN=C=NCC.[S:19]1[CH:23]=[CH:22][C:21]2[C:24]([NH2:28])=[CH:25][CH:26]=[CH:27][C:20]1=2.[N:29]1([C:35]2[N:36]=[C:37]([CH2:42][C:43]([O-])=[O:44])[NH:38][C:39](=[O:41])[CH:40]=2)[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.[Na+]>CN(C)C=O>[S:19]1[C:20]2[CH:27]=[CH:26][CH:25]=[C:24]([NH:28][C:43](=[O:44])[CH2:42][C:37]3[NH:38][C:39](=[O:41])[CH:40]=[C:35]([N:29]4[CH2:34][CH2:33][O:32][CH2:31][CH2:30]4)[N:36]=3)[C:21]=2[CH:22]=[CH:23]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049PyridineHCID 298484Benzo(b)thiophen-4-ylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 136041844Sodium (4-morpholin-4-yl-6-oxo-1,6-dihydropyrimidin-2-yl)acetate

Product 1

HCID 136352208HCID 136352208, compoundYield 73.9%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Procedure

2 ml of pyridine, 257 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride and 223 mg of benzo[B]thiophen-4-ylamine are added to a solution of 250 mg of sodium [4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetate prepared in stage 2 of example 1, in 2 ml of N,N-dimethylformamide. The reaction mixture is stirred at ambient temperature for 15 hours, and then concentrated under reduced pressure. Water and ethyl acetate are added and the resulting mixture is thus stirred for 30 minutes. The precipitate formed is filtered off, and rinsed with water, ethyl ether and petroleum ether. The solid obtained is dried under vacuum. 262 mg of N-(1-benzothiophen-4-yl)-2-[4-(morpholin-4-yl)-6-oxo-1,6-dihydropyrimidin-2-yl]acetamide are obtained in the formed of an off-white solid, the characteristics of which are the following:

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionWater and ethyl acetate are added
  3. stirringthe resulting mixture is thus stirred for 30 minutes
  4. customThe precipitate formed
  5. filtrationis filtered off
  6. washrinsed with water, ethyl ether and petroleum ether
  7. customThe solid obtained
  8. customis dried under vacuum

Sources & evidence

ORD record
ord-fe84703a600848f4b2d1a8b13699b42b
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791255B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes