3-(Bromomethyl)-4-methyl-1,2,5-oxadiazole → 5-tert-Butyl-3-(4-methyl-furazan-3-ylmethyl)-7-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 400945Notes

Reaction equation

HRID 400945 reaction equation
C(C1N=C(N2CCC(F)(F)C2)C2N=NN(CC)C=2N=1)(C)(C)C.[C:23]([C:27]1[N:28]=[C:29]([N:36]2[CH2:42][C:38]3([CH2:41][O:40][CH2:39]3)[CH2:37]2)[C:30]2[N:35]=[N:34][NH:33][C:31]=2[N:32]=1)([CH3:26])([CH3:25])[CH3:24].Br[CH2:44][C:45]1[C:49]([CH3:50])=[N:48][O:47][N:46]=1>>[C:23]([C:27]1[N:28]=[C:29]([N:36]2[CH2:37][C:38]3([CH2:39][O:40][CH2:41]3)[CH2:42]2)[C:30]2[N:35]=[N:34][N:33]([CH2:44][C:45]3[C:49]([CH3:50])=[N:48][O:47][N:46]=3)[C:31]=2[N:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 3

HCID 198327413-(Bromomethyl)-4-methyl-1,2,5-oxadiazoleHCID 715582055-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178441781HCID 178441781, compound

Product 1

HCID 866833565-tert-Butyl-3-(4-methyl-furazan-3-ylmethyl)-7-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3-ethyl-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 61), the title compound was prepared from 5-tert-Butyl-7-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and 3-(bromomethyl)-4-methyl-1,2,5-oxadiazole and isolated as white solid. MS (m/e): 371.3 (MH+).

Workup

  1. customisolated as white solid

Sources & evidence

ORD record
ord-e6608af3a85d45fbaa9b908c97aacc5c
Source dataset
uspto-grants-2014_06
Patent number
US08741906B2

Reaction notes

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