2-(Chloromethyl)-5-methyl-1,3,4-oxadiazole → HCID 89586455, compound

HRID 2179078Notes

Reaction equation

HRID 2179078 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:21]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22]2)[C:8]2[C:9](=[N:11][N:12]([CH2:14][C:15]3C(C)=NO[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)C2)C2N=NNC=2N=1)(C)(C)C.Cl[CH2:53][C:54]1[O:55]C(C)=N[N:58]=1>>[C:1]([C:5]1[N:6]=[C:7]([N:21]2[CH2:25][CH2:24][C@H:23]([OH:26])[CH2:22]2)[C:8]2[C:9](=[N:11][N:12]([CH2:14][C:15]3[O:55][C:54]([CH3:53])=[N:58][N:16]=3)[N:13]=2)[N:10]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 3

HCID 38266202-(Chloromethyl)-5-methyl-1,3,4-oxadiazoleHCID 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 178441791HCID 178441791, compound

Product 1

HCID 89586455HCID 89586455, compound

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 2-(chloromethyl)-5-methyl-1,3,4-oxadiazole and isolated as light yellow gum. MS (m/e): 359.5 (MH+).

Workup

  1. customisolated as light yellow gum

Sources & evidence

ORD record
ord-6f8ff39fc622436eac91f7e904ae4aaa
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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