Morpholine → 5-(6-Morpholinohexanamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

HRID 512557Notes

Reaction equation

Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[S:14][C:13]([NH:15][C:16]2[CH:25]=[CH:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:17]=2)=[N:12][C:11]=1[C:26]([NH2:28])=[O:27])=[O:8].[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1>CC(N(C)C)=O>[O:32]1[CH2:33][CH2:34][N:29]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]2[S:14][C:13]([NH:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:17]=3)=[N:12][C:11]=2[C:26]([NH2:28])=[O:27])=[O:8])[CH2:30][CH2:31]1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 5-(6-bromohexanamido)-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (150 mg, 0.32 mmol) and morpholine (0.06 mL, 0.69 mmol) in DMA (0.5 ml) was heated at 120° C. for 1.5 hrs in a sealed tube. The reaction mixture was then diluted with ice-water. The resulting solids were collected by filtration and washed successively with ether and MeOH to give 135 mg (90% yield) of the titled compound.

Workup

filtrationThe resulting solids were collected by filtration
washwashed successively with ether and MeOH

Sources & evidence

ORD record: ord-267ecfdc4f0b442ab1ebd4d3f9405709
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102637B2

Reaction notes

Loading…