Dimethyl Sulfoxide → 2-Amino-nicotinic acid N'-(2-(4-benzyloxy-phenyl)-acetyl)-hydrazide

HRID 1927231Notes

Reaction equation

HRID 1927231 reaction equation
CS(C)=O.[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][NH2:23])=[O:21])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:24][C:25]1[N:33]=[CH:32][CH:31]=[CH:30][C:26]=1[C:27](O)=[O:28].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>O.C(N(CC)CC)C>[CH2:5]([O:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([NH:22][NH:23][C:27](=[O:28])[C:26]2[CH:30]=[CH:31][CH:32]=[N:33][C:25]=2[NH2:24])=[O:21])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 729302-Aminonicotinic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59287387(4-Benzyloxy-phenyl)-acetic acid hydrazide

Product 1

HCID 592873892-Amino-nicotinic acid N'-(2-(4-benzyloxy-phenyl)-acetyl)-hydrazideYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of DMSO (3 mL) of (4-benzyloxy-phenyl)-acetic acid hydrazide (130 mg) described in Manufacturing Example 8-1 were added triethylamine (0.21 mL), 2-aminonicotinic acid (70 mg), and BOP reagent (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) (250 mg), which was stirred for 1 hour at the same temperature. Water was added to the reaction solution, and the solids thus precipitated were filtered off to obtain the titled compound (170 mg).

Workup

  1. customthe solids thus precipitated
  2. filtrationwere filtered off

Sources & evidence

ORD record
ord-c4b0f9293ee745e0bd242867d9106980
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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