Tributylamine → Capadenoson

HRID 2214973Notes

Reaction equation

HRID 2214973 reaction equation
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:16]=[CH:15][C:8]([CH:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12])=[CH:7][CH:6]=1.[C:17]([CH2:19][C:20]([NH2:22])=[S:21])#[N:18].Cl[CH2:24][C:25]1[N:26]=[C:27]([C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=2)[S:28][CH:29]=1.C(N(CCCC)CCCC)CCC>CO>[NH2:12][C:11]1[C:10]([C:13]#[N:14])=[C:9]([C:8]2[CH:15]=[CH:16][C:5]([O:4][CH2:3][CH2:2][OH:1])=[CH:6][CH:7]=2)[C:19]([C:17]#[N:18])=[C:20]([S:21][CH2:24][C:25]2[N:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[S:28][CH:29]=2)[N:22]=1

Participants

6

Reactant 4

HCID 7622TributylamineHCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazoleHCID 14162772-CyanoethanethioamideHCID 21949078p-(2-Hydroxyethoxy)benzylideneMalononitrile

Product 1

HCID 9936489Capadenoson

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

428.4 g (2.0 mol) of 2-[4-(2-hydroxyethoxy)-benzylidene]malononitrile, 108.4 g (1.05 mol) of 2-cyanothioacetamide and 244.1 g (1.0 mol) of 4-chloromethyl-2-(4-chlorophenyl)-1,3-thiazole are suspended in 3.4 liters of methanol and 556.1 g (3.0 mol) of tributylamine are added over a period of 60 minutes. The mixture is subsequently stirred for 20 hours at room temperature and the product is filtered off. After drying in vacuo, the crude product (360.8 g, crude yield: 70% of theory) is suspended in 3 liters of dichloromethane and stirred for 2 hours at 35° C. The product is filtered off and dried in a high vacuum. The crystals, which are now white, can be purified further by recrystallization from tetrahydrofuran/water (1:1).

Workup

  1. filtrationthe product is filtered off
  2. customAfter drying in vacuo
  3. stirringstirred for 2 hours at 35° C
  4. filtrationThe product is filtered off
  5. customdried in a high vacuum
  6. customcan be purified further by recrystallization from tetrahydrofuran/water (1:1)

Sources & evidence

ORD record
ord-9bb00e2e4b154ab6a7ca1bcfda77b5ee
Source dataset
uspto-grants-2006_09
Patent number
US07109218B2

Reaction notes

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