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

HRID 2179069Notes

Reaction equation

HRID 2179069 reaction equation
C(C1N=C(N2CC[C@H](O)C2)C2C(=NN(CC3C(C)=NON=3)N=2)N=1)(C)(C)C.[C:27]([C:31]1[N:32]=[C:33]([N:40]2[CH2:44][CH2:43][C@H:42]([O:45]C(=O)C(F)(F)F)[CH2:41]2)[C:34]2[N:39]=[N:38][NH:37][C:35]=2[N:36]=1)([CH3:30])([CH3:29])[CH3:28].Br.Br[CH2:54][C:55]1[C:56]([Cl:61])=[N:57][CH:58]=[CH:59][CH:60]=1>>[C:27]([C:31]1[N:32]=[C:33]([N:40]2[CH2:44][CH2:43][C@H:42]([OH:45])[CH2:41]2)[C:34]2[C:35](=[N:37][N:38]([CH2:54][C:55]3[C:56]([Cl:61])=[N:57][CH:58]=[CH:59][CH:60]=3)[N:39]=2)[N:36]=1)([CH3:29])([CH3:28])[CH3:30]

Participants

4

Reactant 3

HCID 71575968(S)-1-[5-tert-Butyl-2-(4-methyl-furazan-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-olHCID 895389403-(Bromomethyl)-2-chloropyridine hydrobromideHCID 178441791HCID 178441791, compound

Product 1

HCID 71575971(S)-1-[5-tert-Butyl-2-(2-chloro-pyridin-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

Procedure

In analogy to the procedure described for the synthesis of (S)-1-[5-tert-Butyl-2-(4-methyl-furazan-3-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol (example 73), the title compound was prepared from Trifluoro-acetic acid (S)-1-(5-tert-butyl-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl)-pyrrolidin-3-yl-ester and 3-(bromomethyl)-2-chloropyridine hydrobromide and isolated as light brown gum. MS (m/e): 388.3 (MH+).

Workup

  1. customisolated as light brown gum

Sources & evidence

ORD record
ord-72d2ea64d340483ba5c4edb67c34198f
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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