Pyridine → 1-{4-[4-Carbamoyl-2-(naphthalen-2-ylamino)thiazol-5-ylcarbamoyl]benzyl}pyridinium chloride

HRID 512537Notes

Reaction equation

HRID 512537 reaction equation
[NH2:1][C:2]1[S:6][C:5]([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[N:4][C:3]=1[C:18]([NH2:20])=[O:19].[Cl:21][CH2:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1.[N:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CN(C1C=CN=CC=1)C>[Cl-:21].[C:18]([C:3]1[N:4]=[C:5]([NH:7][C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)[S:6][C:2]=1[NH:1][C:27]([C:26]1[CH:30]=[CH:31][C:23]([CH2:22][N+:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:24][CH:25]=1)=[O:28])(=[O:19])[NH2:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 701364-(Chloromethyl)benzoyl chlorideHCID 867033695-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

Product 1

HCID 725504131-{4-[4-Carbamoyl-2-(naphthalen-2-ylamino)thiazol-5-ylcarbamoyl]benzyl}pyridinium chlorideYield 10%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

To a solution of 5-amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (0.18 g, 0.62 mmol) and a catalytic amount of DMAP in pyridine (5 mL) was added 4-chloromethylbenzoyl chloride (0.13 g, 0.68 mmol) at 0° C. under N2-atmosphere. The mixture was stirred for 16 hrs at rt under nitrogen atmosphere. The solvent was evaporated, and the residue was triturated with water. The resulting solids were collected by filtration and washed with MeOH to give 0.030 g (10% yield) of the titled compound.

Workup

  1. customThe solvent was evaporated
  2. customthe residue was triturated with water
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with MeOH

Sources & evidence

ORD record
ord-21134be9d76349748d92a51f4857407e
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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