3-(Chloromethyl)-5-methyl-1,2,4-oxadiazole → HCID 71576039, compound

HRID 2179077Notes

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)=N[O:17][N:16]=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[C:27]([C:31]1[N:32]=C(N2CC[C@H](OC(=O)C(F)(F)F)C2)C2N=NNC=2N=1)(C)(C)C.ClCC1N=C(C)ON=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[N:32]=[C:31]([CH3:27])[O:17][N:16]=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 3021573-(Chloromethyl)-5-methyl-1,2,4-oxadiazole

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-ol

HCID 178441791HCID 178441791, compound

Product 1

HCID 71576039HCID 71576039, 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 3-(chloromethyl)-5-methyl-1,2,4-oxadiazole and isolated as light yellow gum. MS (m/e): 359.5 (MH+).

Workup

customisolated as light yellow gum

Sources & evidence

ORD record: ord-0f0153eb8b5244009f7efe9c2ddf3851
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067943B2

Reaction notes

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