Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine → HCID 67388898, compound

HRID 908439Notes

Reaction equation

HRID 908439 reaction equation
O[C@H]([C@@H]1C([O-])=C(O)C(=O)O1)CO.[Na+].C(N1C=C(CN(CC2N=NN(CC3C=CC=CC=3)C=2)CC2N=NN(CC3C=CC=CC=3)C=2)N=N1)C1C=CC=CC=1.[O:54]1[C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=2[N:56]=[C:55]1[C:63]1[C:64]([NH2:71])=[N:65][CH:66]=[C:67]([C:69]#[CH:70])[CH:68]=1.[N:72]([CH:75]1[CH2:80][CH2:79][N:78]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:77][CH2:76]1)=[N+:73]=[N-:74]>C1COCC1.CC#N.CC#N.CC#N.CC#N.F[P-](F)(F)(F)(F)F.[Cu+].O>[NH2:71][C:64]1[N:65]=[CH:66][C:67]([C:69]2[N:74]=[N:73][N:72]([CH:75]3[CH2:76][CH2:77][N:78]([C:81]([O:83][C:84]([CH3:87])([CH3:86])[CH3:85])=[O:82])[CH2:79][CH2:80]3)[CH:70]=2)=[CH:68][C:63]=1[C:55]1[O:54][C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][C:57]=2[N:56]=1

Participants

8

Reactant 4

HCID 11203363Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amineHCID 114587941,1-Dimethylethyl 4-azido-1-piperidinecarboxylateHCID 23667548Sodium AscorbateHCID 86630153HCID 86630153, compound

Product 1

HCID 67388898HCID 67388898, compoundYield 88.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 11068737tetrakis(acetonitrile)copper(I) hexafluorophosphateSolvent

Procedure

Sodium (R)-2-((S)-1,2-dihydroxyethyl)-4-hydroxy-5-oxo-2,5-dihydrofuran-3-olate (211 mg) and tris((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amine (90 mg) were added to a stirred solution of 3-(1,3-benzoxazol-2-yl)-5-ethynyl-pyridin-2-amine (125 mg) in THF (15 ml) at room temperature. To the reaction mixture was then added water (5 ml), tert-butyl 4-azidopiperidine-1-carboxylate (180 mg) in THF (1 ml) and tetrakis(acetonitrile)copper(I) hexafluorophosphate (9.9 mg). The resulting solution was stirred overnight: a precipitate appeared. The precipitate was filtered, washed successively with water, THF, diethyl ether and petroleum ether, and dried under vacuum at 50° C. to afford tert-butyl 4-[4-[6-amino-5-(1,3-benzoxazol-2-yl)-3-pyridyl]triazol-1-yl]piperidine-1-carboxylate (218 mg) as a solid; NMR Spectrum: (DMSOd6) 1.44 (s, 9H), 1.82-1.96 (m, 2H), 2.07-2.21 (m, 2H), 3.01 (bs, 2H), 3.99-4.20 (m, 2H), 4.72-4.85 (m, 1H), 7.40-7.53 (m, 2H), 7.80-8.04 (m, 4H), 8.72 (s, 2H), 8.78 (s, 1H); Mass spectrum: M+H+: 462

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed successively with water, THF, diethyl ether and petroleum ether
  3. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-c248eff5a3e34b3f970ca8e543cc5314
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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