Chloroform → HCID 86707543, compound

HRID 339057Notes

Reaction equation

HRID 339057 reaction equation
C(Cl)(Cl)Cl.CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:48]1[CH:49]=[CH:50][CH:51]=[C:52]2[C:57]=1[N:56]=[C:55]([C:58]1[N:62]3[CH:63]=[C:64]([C@@H:67]([N:72]4[CH2:76][CH2:75][C@H:74]([NH:77][C:78](=[O:84])[O:79][C:80]([CH3:83])([CH3:82])[CH3:81])[CH2:73]4)[C:68]([F:71])([F:70])[F:69])[CH:65]=[CH:66][C:61]3=[N:60][N:59]=1)[CH:54]=[CH:53]2.[CH2:85]([SH:87])[CH3:86].C(N(C(C)C)C(C)C)C>O1CCOCC1>[CH2:85]([S:87][C:48]1[CH:49]=[CH:50][CH:51]=[C:52]2[C:57]=1[N:56]=[C:55]([C:58]1[N:62]3[CH:63]=[C:64]([C@@H:67]([N:72]4[CH2:76][CH2:75][C@H:74]([NH:77][C:78](=[O:84])[O:79][C:80]([CH3:83])([CH3:82])[CH3:81])[CH2:73]4)[C:68]([F:71])([F:70])[F:69])[CH:65]=[CH:66][C:61]3=[N:60][N:59]=1)[CH:54]=[CH:53]2)[CH3:86]

Participants

7

Reactant 5

HCID 6212ChloroformHCID 6343EthanethiolHCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 86707544HCID 86707544, compound

Product 1

HCID 86707543HCID 86707543, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

CHCl3 (8.75 mg, 0.00845 mmol), (9,9-dimethyl-9H-xanthene-4,5-diyl)bis(diphenylphosphine) (9.78 mg, 0.0169 mmol), tert-butyl (S)-1-((R)-1-(3-(8-bromo quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (100 mg, 0.169 mmol), ethanethiol (31.5 mg, 0.507 mmol) and N-ethyl-N-isopropylpropan-2-amine (131 mg, 1.01 mmol) in dioxane were heated to 150° C. under microwave irradiation for 1 hour. After cooling, the reaction was concentrated under reduced pressure and purified by chromatography (SP4, 12M, eluting with a gradient of water/ACN 100:0 to 0:100, 30 column volumes) to yield tert-butyl (S)-1-((R)-1-(3-(8-(ethylthio)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)-2,2,2-trifluoroethyl)pyrrolidin-3-ylcarbamate (60 mg, 62.0% yield)

Workup

  1. temperatureAfter cooling
  2. concentrationthe reaction was concentrated under reduced pressure
  3. custompurified by chromatography (SP4, 12M
  4. washeluting with a gradient of water/ACN 100:0 to 0:100, 30 column volumes)

Sources & evidence

ORD record
ord-0c43841c2edf41e4be12d694ebf641c9
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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