1-(Bromomethyl)-2-(trifluoromethyl)benzene → (S)-1-[5-(2,2,2-Trifluoro-ethoxy)-2-(2-trifluoromethyl-benzyl)-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol

HRID 2179105Notes

Reaction equation

HRID 2179105 reaction equation
C(C1N=C(N2CCC(F)(F)C2)C2C(=NN(CC)N=2)N=1)(C)(C)C.[F:23][C:24]([F:43])([F:42])[CH2:25][O:26][C:27]1[N:28]=[C:29]([N:36]2[CH2:40][CH2:39][C@H:38]([OH:41])[CH2:37]2)[C:30]2[N:35]=[N:34][NH:33][C:31]=2[N:32]=1.Br[CH2:45][C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=1[C:52]([F:55])([F:54])[F:53]>>[F:43][C:24]([F:42])([F:23])[CH2:25][O:26][C:27]1[N:28]=[C:29]([N:36]2[CH2:40][CH2:39][C@H:38]([OH:41])[CH2:37]2)[C:30]2[C:31](=[N:33][N:34]([CH2:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][C:47]=3[C:52]([F:53])([F:54])[F:55])[N:35]=2)[N:32]=1

Participants

4

Reactant 3

HCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 715763075-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178521640HCID 178521640, compound

Product 1

HCID 71576248(S)-1-[5-(2,2,2-Trifluoro-ethoxy)-2-(2-trifluoromethyl-benzyl)-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 5-tert-butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidine (example 3, step b), the title compound was prepared from (S)-1-[5-(2,2,2-Trifluoro-ethoxy)-3H-[1,2,3]triazolo[4,5-d]pyrimidin-7-yl]-pyrrolidin-3-ol and 1-(bromomethyl)-2-(trifluoromethyl)benzene. MS (m/e): 463.4 (MH+).

Sources & evidence

ORD record
ord-f21b2c7804ba44958185b077a698c169
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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