1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,6-Diamino-nicotinic acid N'-(2-(4-benzyloxy-phenyl)-acetyl)-hydrazide

HRID 1927232Notes

Reaction equation

HRID 1927232 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][NH2:19])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[N:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:22]=1[C:23](O)=[O:24].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>O.C(N(CC)CC)C.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16]([NH:18][NH:19][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][C:28]([NH2:30])=[N:29][C:21]=2[NH2:20])=[O:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 189772452,6-Diaminonicotinic acidHCID 59287387(4-Benzyloxy-phenyl)-acetic acid hydrazide

Product 1

HCID 592873832,6-Diamino-nicotinic acid N'-(2-(4-benzyloxy-phenyl)-acetyl)-hydrazideYield 66.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a solution of DMF (1 mL) of (4-benzyloxy-phenyl)-acetic acid hydrazide (46 mg) described in Manufacturing Example 8-1 were added triethylamine (0.10 mL), 2,6-diamino-nicotinic acid (30 mg) described in Manufacturing Example 10-2-4, HOBt (27 mg), and WSC (41 mg), which was stirred overnight at the same temperature. Water was added to the reaction solution, and the precipitated solids were filtered off to obtain the titled compound (47 mg) as a crude form. This compound was used directly as a crude form in the subsequent reaction.

Workup

  1. filtrationthe precipitated solids were filtered off

Sources & evidence

ORD record
ord-fcc31a2ab1984755b1b53c0f3dec231f
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

Loading…