HCID 86656417, compound → HCID 178467402, compound

HRID 1027500Notes

Reaction equation

HRID 1027500 reaction equation
[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[N:8]=[C:9]([O:29][CH2:30][CH3:31])[C:10]3[N:15]=[C:14]([C:16]4[CH:21]=[C:20]([CH3:22])[C:19]([O:23][CH2:24][CH:25]5[CH2:27][O:26]5)=[C:18]([CH3:28])[CH:17]=4)[O:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1.[CH:34]([C:37]1[NH:38][C:39]([SH:42])=[N:40][N:41]=1)([CH3:36])[CH3:35]>CN(C)C=O>[Cl:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][C:7]2[N:8]=[C:9]([O:29][CH2:30][CH3:31])[C:10]3[N:15]=[C:14]([C:16]4[CH:21]=[C:20]([CH3:22])[C:19]([O:23][CH2:24][CH:25]([OH:26])[CH2:27][S:42][C:39]5[NH:38][C:37]([CH:34]([CH3:36])[CH3:35])=[N:41][N:40]=5)=[C:18]([CH3:28])[CH:17]=4)[O:13][C:11]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 86656417HCID 86656417, compoundHCID 178440401HCID 178440401, compound

Product 1

HCID 178467402HCID 178467402, compoundYield 22.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 300 mg of 5-(4-chloro-benzyl)-2-(3,5-dimethyl-4-oxiranylmethoxy-phenyl)-7-ethoxy-oxazolo[5,4-d]pyrimidine (prepared analogously as described in example 20, step (a)) and 92 mg of 5-isopropyl-4H-[1,2,4]triazole-3-thiol in 3 ml of dimethylformamide was heated for 2 h to 130° C. in a microwave reactor. After removal of the solvent the product was isolated by preparative HPLC (method HPLC1) to yield 89 mg of the title compound.

Workup

  1. temperaturewas heated for 2 h to 130° C. in a microwave reactor
  2. customAfter removal of the solvent the product
  3. customwas isolated by preparative HPLC (method HPLC1)

Sources & evidence

ORD record
ord-b483d67a14e24978a65ecf29c6df2af0
Source dataset
uspto-grants-2014_05
Patent number
US08735387B2

Reaction notes

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