5-(chloromethyl)-1-cyclopropyl-1H-1,2,3,4-tetrazole → (S)-1-[5-tert-Butyl-2-(1-cyclopropyl-1H-tetrazol-5-ylmethyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2179084Notes

Reaction equation

HRID 2179084 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:33](N2CC[C@H](OC(=O)C(F)(F)F)C2)[C:34]2[N:39]=[N:38][NH:37][C:35]=2N=1)(C)(C)C.ClCC1N(C2CC2)N=NN=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:37]([CH:35]4[CH2:33][CH2:34]4)[N:38]=[N:39][N:16]=3)[N:13]=2)[N:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 255244995-(chloromethyl)-1-cyclopropyl-1H-1,2,3,4-tetrazoleHCID 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 89586333(S)-1-[5-tert-Butyl-2-(1-cyclopropyl-1H-tetrazol-5-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 5-(chloromethyl)-1-cyclopropyl-1H-tetrazole and isolated as light yellow gum. MS (m/e): 385.3 (MH+).

Workup

  1. customisolated as light yellow gum

Sources & evidence

ORD record
ord-4aecefe54fc748faaddd43eeac93c925
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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