1-Hydroxybenzotriazole → 2,6-Diamino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamide

HRID 2080186Notes

Reaction equation

HRID 2080186 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.Cl.C(N=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.[CH2:34]([C:41]1[S:45][C:44]([CH2:46][NH2:47])=[CH:43][CH:42]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CS(C)=O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:47][CH2:46][C:44]1[S:45][C:41]([CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:42][CH:43]=1)=[O:6]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189772452,6-Diaminonicotinic acidHCID 231306122-Thiophenemethanamine,5-(phenylmethyl)-

Product 1

HCID 231303582,6-Diamino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamideYield 30%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 2,6-diaminonicotinic acid described in Preparation Example A-15 (173 mg, 1.13 mmol) in dimethylsulfoxide (15 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (433 mg, 2.26 mmol), 1-hydroxybenzotriazole (346 mg, 2.26 mmol) and C-(5-benzyl-thiophen-2-yl)-methylamine described in Preparation Example 42 (230 mg, 1.13 mmol), and the solution was stirred at room temperature fro 16 hours 30 minutes. The reaction solution was poured into brine, the solution was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate and then concentrated. The obtained residue was subjected to NH silica gel column chromatography, eluted with solvent (ethyl acetate) and the title compound (114 mg, 0.34 mmol, 30%) was obtained.

Workup

  1. extractionthe solution was extracted with ethyl acetate
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. washeluted with solvent (ethyl acetate)

Sources & evidence

ORD record
ord-66fafe050d8140739905096af590ecdc
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

Loading…