p-Toluenesulfonic acid → (2-[1,2,3] Triazol-1-yl-ethyl)-(4-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4ylmethoxy}-benzyl)-amine

HRID 750948Notes

Reaction equation

HRID 750948 reaction equation
[F:1][C:2]([F:29])([F:28])[S:3]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[C:13]2[O:14][CH:15]=[C:16]([CH2:18][O:19][C:20]3[CH:27]=[CH:26][C:23]([CH:24]=O)=[CH:22][CH:21]=3)[N:17]=2)=[CH:7][CH:6]=1)=[O:4].[N:30]1([CH2:35][CH2:36][NH2:37])[CH:34]=[CH:33][N:32]=[N:31]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([BH3-])#N.[Na+]>CO>[N:30]1([CH2:35][CH2:36][NH:37][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH2:18][C:16]3[N:17]=[C:13](/[CH:12]=[CH:11]/[C:8]4[CH:9]=[CH:10][C:5]([S:3]([C:2]([F:29])([F:1])[F:28])=[O:4])=[CH:6][CH:7]=4)[O:14][CH:15]=3)=[CH:21][CH:22]=2)[CH:34]=[CH:33][N:32]=[N:31]1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 5003444Sodium cyanoborohydrideHCID 225619722-(1H-1,2,3-Triazol-1-yl)ethanamineHCID 866005604-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzaldehyde

Product 1

HCID 11364348(2-[1,2,3] Triazol-1-yl-ethyl)-(4-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4ylmethoxy}-benzyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 120 mg (0.28 mmol) 4-{2-[(E)-2-(4-trifluoromethanesulfinyl-phenyl)-vinyl]-oxazol-4-ylmethoxy}-benzaldehyde, 31 mg (0.28 mmol) (2-[1,2,3]triazol-1-yl-ethyl)-amine and 5 mg toluene-4-sulfonic acid in 10 ml methanol was stirred at room temperature for 1 hour, then 18 mg (0.28 mmol) sodium cyanoborohydride was added and the mixture stirred over night. After evaporation and chromatography on silica with ethyl acetate/methanolic ammonia 85:15, the title compound was isolated as light yellow solid melting at 111-113° C.; yield 89 mg (60%).

Workup

  1. customAfter evaporation and chromatography on silica with ethyl acetate/methanolic ammonia 85:15

Sources & evidence

ORD record
ord-1b585942a8c84584b5e8b6ff11ed6e6f
Source dataset
uspto-grants-2008_07
Patent number
US07405231B2

Reaction notes

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