N-(3,5-Bis(hydroxymethyl)phenyl)-1-((3,4-dichlorophenyl)methyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide → {5-[({1-[(3,4-Dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}methyl)amino]benzene-1,3-diyl}dimethanol

HRID 450523Notes

Reaction equation

HRID 450523 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[N:15]=[N:16][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[C:23]([Cl:28])[CH:22]=3)[C:18]=2[CH3:19])=O)[CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=1>C(#N)C>[Cl:28][C:23]1[CH:22]=[C:21]([CH2:20][N:17]2[C:18]([CH3:19])=[C:14]([CH2:12][NH:11][C:5]3[CH:6]=[C:7]([CH2:9][OH:10])[CH:8]=[C:3]([CH2:2][OH:1])[CH:4]=3)[N:15]=[N:16]2)[CH:26]=[CH:25][C:24]=1[Cl:27]

Participants

3

Reactant 1

HCID 42603248N-(3,5-Bis(hydroxymethyl)phenyl)-1-((3,4-dichlorophenyl)methyl)-5-methyl-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 42603357{5-[({1-[(3,4-Dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}methyl)amino]benzene-1,3-diyl}dimethanolYield 5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was obtained as a by product of the reduction of dimethyl 5-[({1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazol-4-yl}carbonyl)amino]-1,3-benzenedicarboxylate (Intermediate 14) in the preparation of N-[3,5-bis(hydroxymethyl)phenyl]-1-[(3,4-dichlorophenyl)methyl]-5-methyl-1H-1,2,3-triazole-4-carboxamide (Example 52). It was obtained as a white solid (5%) via recrystallisation from acetonitrile. HRMS calculated for C19H20Cl2N4O2 (M+H)+407.1042, found: 407.1022, Rt: 2.40 min. MP: 120° C.

Sources & evidence

ORD record
ord-8605b3960797484dbc35f55c7837a01d
Source dataset
uspto-grants-2013_07
Patent number
US08486977B2

Reaction notes

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