Water → Neladenoson

HRID 1621320Notes

Reaction equation

HRID 1621320 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([S:22][CH2:23][C:24]2[N:25]=[C:26]([C:29]3[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=3)[S:27][CH:28]=2)[N:3]=1.[NH:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1.O>C1COCC1>[Cl:35][C:32]1[CH:31]=[CH:30][C:29]([C:26]2[S:27][CH:28]=[C:24]([CH2:23][S:22][C:4]3[C:5]([C:20]#[N:21])=[C:6]([C:10]4[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][OH:19])=[CH:12][CH:11]=4)[C:7]([C:8]#[N:9])=[C:2]([N:36]4[CH2:40][CH2:39][CH2:38][CH2:37]4)[N:3]=3)[N:25]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 31268PyrrolidineHCID 866438472-Chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile

Product 1

HCID 46847262Neladenoson

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

At RT, 90 mg (0.17 mmol) of 2-chloro-6-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-4-(4-(2-hydroxyethoxy)phenyl)pyridine-3,5-dicarbonitrile (Example 2A) and 30 μl (0.37 mmol) of pyrrolidine were stirred in 2.3 ml of THF for 30 min. About 12 ml of water were added to the reaction mixture, the suspension formed was freed from THF on a rotary evaporator, and the precipitate formed was filtered off and washed with water and dried under high vacuum. This gave 78 mg (81% of theory) of the desired target compound.

Workup

  1. customthe suspension formed
  2. customwas freed from THF on a rotary evaporator
  3. customthe precipitate formed
  4. filtrationwas filtered off
  5. washwashed with water
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-11c263d61ec140748130b77d936e631a
Source dataset
uspto-grants-2014_07
Patent number
US08772498B2

Reaction notes

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