3-(Bromomethyl)-4-methyl-1,2,5-oxadiazole → (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

HRID 2179065Notes

Reaction equation

HRID 2179065 reaction equation
C(C1N=C(N2CCC(F)(F)C2)C2C(=NN(CC)N=2)N=1)(C)(C)C.[C:23]([C:27]1[N:28]=[C:29]([N:36]2[CH2:40][CH2:39][C@H:38]([O:41]C(=O)C(F)(F)F)[CH2:37]2)[C:30]2[N:35]=[N:34][NH:33][C:31]=2[N:32]=1)([CH3:26])([CH3:25])[CH3:24].Br[CH2:49][C:50]1[C:54]([CH3:55])=[N:53][O:52][N:51]=1>CO>[C:23]([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]([CH2:49][C:50]3[C:54]([CH3:55])=[N:53][O:52][N:51]=3)[N:35]=2)[N:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

5

Reactant 3

HCID 198327413-(Bromomethyl)-4-methyl-1,2,5-oxadiazoleHCID 715763075-tert-Butyl-7-(3,3-difluoro-pyrrolidin-1-yl)-2-ethyl-2H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178441791HCID 178441791, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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 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)-4-methyl-1,2,5-oxadiazole. After completion of the substitution reaction methanol was added and the mixture was stirred for 1 h at room temperature and subsequently subjected to purification with preparative HPLC on reversed phase eluting with a gradient formed from acetonitrile, water and NEt3. After evaporation of the product containing fractions the title compound was isolated as light-yellow gum. MS (m/e): 359.3 (MH+).

Workup

  1. additionwas added
  2. customsubsequently subjected to purification with preparative HPLC on reversed phase
  3. washeluting with a gradient
  4. customformed from acetonitrile, water and NEt3
  5. customAfter evaporation of the product
  6. additioncontaining fractions the title compound
  7. customwas isolated as light-yellow gum

Sources & evidence

ORD record
ord-f1e0f667f976457bb515cc4714e02887
Source dataset
uspto-grants-2015_06
Patent number
US09067943B2

Reaction notes

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