Pyridine → 5-(6-Bromohexanamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

HRID 512556Notes

Reaction equation

HRID 512556 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7](Cl)=[O:8].[NH2:10][C:11]1[S:15][C:14]([NH:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[N:13][C:12]=1[C:27]([NH2:29])=[O:28].N1C=CC=CC=1>C1COCC1>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:10][C:11]1[S:15][C:14]([NH:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)=[N:13][C:12]=1[C:27]([NH2:29])=[O:28])=[O:8]

Participants

5

Reactant 3

HCID 1049PyridineHCID 898486-Bromohexanoyl chlorideHCID 867033695-Amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

Product 1

HCID 867033885-(6-Bromohexanamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamideYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 6-bromohexanoyl chloride (0.82 mL, 5.28 mmol) in THF (4 mL) was added dropwise to a mixture of 5-amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (0.30 g, 1.06 mmol) and pyridine (4 mL) in THF (20 mL) at 0° C., and the mixture was stirred for 16 hrs at rt. The reaction mixture was quenched with ice-water. The resulting solids were collected by filtration and washed with ether and EtOAc to give 0.45 g (92% yield) of the titled compound.

Workup

  1. customThe reaction mixture was quenched with ice-water
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed with ether and EtOAc

Sources & evidence

ORD record
ord-c82854bffd4c4f8692f643262730a683
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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