(1R)-1-(2-chlorophenyl)ethan-1-ol → 5-tert-Butyl-3-[(S)-1-(2-chloro-phenyl)-ethyl]-7-(3,3-difluoro-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

HRID 2173561Notes

Reaction equation

HRID 2173561 reaction equation
[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:27][CH2:26][C:25]([F:29])([F:28])[CH2:24]2)[C:8]2[NH:13][N:12]([C@@H](C3C=CC=CC=3Cl)C)[NH:11][C:9]=2[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C(C1N=C(N2CCC(F)(F)C2)C2N=NNC=2N=1)(C)(C)C.[Cl:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][C:52]=1[C@H:57](O)[CH3:58]>>[C:1]([C:5]1[N:6]=[C:7]([N:23]2[CH2:27][CH2:26][C:25]([F:28])([F:29])[CH2:24]2)[C:8]2[N:13]=[N:12][N:11]([C@H:57]([C:52]3[CH:53]=[CH:54][CH:55]=[CH:56][C:51]=3[Cl:50])[CH3:58])[C:9]=2[N:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 6999092(1R)-1-(2-chlorophenyl)ethan-1-olHCID 866833045-tert-Butyl-2-[(R)-1-(2-chloro-phenyl)-ethyl]-7-(3,3-difluoro-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidineHCID 178441789HCID 178441789, compound

Product 1

HCID 715586785-tert-Butyl-3-[(S)-1-(2-chloro-phenyl)-ethyl]-7-(3,3-difluoro-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine

Procedure

In analogy to the procedure described for the synthesis of 5-tert-butyl-2-[(R)-1-(2-chloro-phenyl)-ethyl]-7-(3,3-difluoro-pyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (example 87), the title compound was prepared from 5-tert-butyl-7-(3,3-difluoropyrrolidin-1-yl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine and (R)-1-(2-chlorophenyl)ethanol and isolated as light-yellow gum (3.8 mg, 21%). MS(m/e): 421.4 (MH+).

Sources & evidence

ORD record
ord-bb14f4fac1e646b3922b1b5d28781d3f
Source dataset
uspto-grants-2015_06
Patent number
US09056866B2

Reaction notes

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