3-(Bromomethyl)-4-methyl-1,2,5-oxadiazole → tert-Butyl-[7-(3,3-difluoro-pyrrolidin-1-yl)-2-(4-methyl-furazan-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]-amine

HRID 2179116Notes

Reaction equation

HRID 2179116 reaction equation
C(C1N=C(N2CCC(F)(F)C2)C2C(=NN(CC)N=2)N=1)(C)(C)C.[C:23]([NH:27][C:28]1[N:29]=[C:30]([N:37]2[CH2:41][CH2:40][C:39]([F:43])([F:42])[CH2:38]2)[C:31]2[N:36]=[N:35][NH:34][C:32]=2[N:33]=1)([CH3:26])([CH3:25])[CH3:24].Br[CH2:45][C:46]1[C:50]([CH3:51])=[N:49][O:48][N:47]=1>>[C:23]([NH:27][C:28]1[N:29]=[C:30]([N:37]2[CH2:41][CH2:40][C:39]([F:42])([F:43])[CH2:38]2)[C:31]2[C:32](=[N:34][N:35]([CH2:45][C:46]3[C:50]([CH3:51])=[N:49][O:48][N:47]=3)[N:36]=2)[N:33]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 3

HCID 198327413-(Bromomethyl)-4-methyl-1,2,5-oxadiazoleHCID 715763075-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178448870HCID 178448870, compound

Product 1

HCID 71576309tert-Butyl-[7-(3,3-difluoro-pyrrolidin-1-yl)-2-(4-methyl-furazan-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]-amine

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine (example 3, step b), the title compound was prepared from tert-Butyl-[7-(3,3-difluoro-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-5-yl]-amine and 3-(bromomethyl)-4-methyl-1,2,5-oxadiazole. MS (m/e): 394.4 (MH+)

Sources & evidence

ORD record
ord-b6a559fd43a04387ad8415c22d641a00
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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