1-Hydroxybenzotriazole → HCID 23130447, compound

HRID 2080187Notes

Reaction equation

HRID 2080187 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]([O:41][C:42]1[S:46][C:45]([CH2:47][NH2:48])=[CH:44][CH:43]=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:48][CH2:47][C:45]1[S:46][C:42]([O:41][CH2:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:43][CH:44]=1)=[O:6]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 189772452,6-Diaminonicotinic acidHCID 23130661C-(5-benzyloxy-thiophen-2-yl)methylamine

Product 1

HCID 23130447HCID 23130447, compoundYield 62%

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 (109 mg, 0.71 mmol) in dimethylsulfoxide (10 mL) were added 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (272 mg, 1.42 mmol), 1-hydroxybenzotriazole (217 mg, 1.42 mmol) and C-(5-benzyloxy-thiophen-2-yl)methylamine described in Example E-76 (156 mg, 0.71 mmol), and the solution was stirred at room temperature for 14 hours. The reaction solution was poured into brine, extracted with ethyl acetate, the fractionated 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 (157 mg, 0.44 mmol, 62%) was obtained.

Workup

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

Sources & evidence

ORD record
ord-72549078f6524b529b0e58a0d90db995
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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