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

HRID 2179088Notes

Reaction equation

HRID 2179088 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:27][CH2:26][C@H:25]([OH:28])[C@@H:24]2[CH2:29][OH:30])[C:8]2[C:9](=[N:11][N:12]([CH2:14][C:15]3N(C4CC4)N=N[N:16]=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(N2CC[C@H](OC(=O)C(F)(F)F)[C@@H]2COC(=O)C(F)(F)F)C2N=NNC=2N=1)(C)(C)C.Br[CH2:65][C:66]1C(C)=N[O:68][N:67]=1>>[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:27][CH2:26][C@H:25]([OH:28])[C@@H:24]2[CH2:29][OH:30])[C:8]2[C:9](=[N:11][N:12]([CH2:14][C:15]3[C:66]([CH3:65])=[N:67][O:68][N:16]=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 198327413-(Bromomethyl)-4-methyl-1,2,5-oxadiazoleHCID 89586566(2S,3S)-1-[5-tert-Butyl-2-(1-cyclopropyl-1H-tetrazol-5-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-2-hydroxymethyl-pyrrolidin-3-olHCID 178441792HCID 178441792, compound

Product 1

HCID 89586543(2S,3S)-1-[5-tert-Butyl-2-(4-methyl-furazan-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-2-hydroxymethyl-pyrrolidin-3-ol

Procedure

In analogy to the procedure described for the synthesis of (2S,3S)-1-[5-tert-Butyl-2-(1-cyclopropyl-1H-tetrazol-5-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-2-hydroxymethyl-pyrrolidin-3-ol (example 97), the title compound was prepared from Trifluoro-acetic acid (2S,3S)-1-(5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-2-(2,2,2-trifluoro-acetoxymethyl)-pyrrolidin-3-yl ester and 3-(bromomethyl)-4-methyl-1,2,5-oxadiazole and isolated as white solid. MS (m/e): 389.3 (MH+).

Workup

  1. customisolated as white solid

Sources & evidence

ORD record
ord-65205202f9b14cc89a5543a0597ca2c4
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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