Benzoic Acid → 1-[4-[2-(Tert-butoxycarbonylamino)pyridin-5-yl]benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine

HRID 1060997Notes

Reaction equation

HRID 1060997 reaction equation
[C:1](O)(=O)[C:2]1[CH:7]=CC=C[CH:3]=1.FC(F)(F)[C:12]([OH:14])=[O:13].[Cl:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([S:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)(=[O:30])=[O:29])[CH:22]=[CH:21]2.ON1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2N=N1.CN1CC[O:51][CH2:50]C1.Cl.CN(C)[CH2:57][CH2:58][CH2:59][N:60]=[C:61]=[N:62]CC.[CH3:66]N(C)C=O>ClCCl>[C:2]([O:14][C:12]([NH:62][C:61]1[CH:66]=[CH:57][C:58]([C:41]2[CH:46]=[CH:45][C:44]([C:50]([N:34]3[CH2:33][CH2:32][N:31]([S:28]([C:23]4[CH:22]=[CH:21][C:20]5[C:25](=[CH:26][CH:27]=[C:18]([Cl:17])[CH:19]=5)[CH:24]=4)(=[O:29])=[O:30])[CH2:36][CH2:35]3)=[O:51])=[CH:43][CH:42]=2)=[CH:59][N:60]=1)=[O:13])([CH3:7])([CH3:3])[CH3:1]

Participants

8

Reactant 6

HCID 243Benzoic AcidHCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22710058HCID 22710058, compound

Product 1

HCID 227094561-[4-[2-(Tert-butoxycarbonylamino)pyridin-5-yl]benzoyl]-4-[(6-chloronaphthalen-2-yl)sulfonyl]piperazineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a mixed solvent of dichloromethane (20 ml) and N,N-dimethylformamide (1 ml), 4-[2-(tert-butoxycarbonyl)amino]pyridin-5-yl]benzoic acid (74 mg) and 1-[(6-chloronaphthalen-2-yl)sulfonyl]piperazine trifluoroacetate (110 mg) were suspended. To the resulting suspension, 1-hydroxybenzotriazole (35 mg) and N-methylmorpholine (34 μl) were added, followed by the addition of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (68 mg) under ice cooling. After stirring at room temperature for 6 hours, the solvent was distilled off. The residue was purified by chromatography on a silica gel column (1% methanol-dichloromethane). The solvent was then distilled off, whereby the title compound (128 mg, 90%) was obtained.

Workup

  1. distillationthe solvent was distilled off
  2. customThe residue was purified by chromatography on a silica gel column (1% methanol-dichloromethane)
  3. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-9ba9bd7221d14b5f8db98e063cafe615
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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