1,4-Dioxane hydrochloride → HCID 69208396, compound

HRID 901967Notes

Reaction equation

HRID 901967 reaction equation
C(OC(=O)[NH:7][CH:8]([C:10]1[S:11][CH:12]=[C:13]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[O:16])[N:14]=1)[CH3:9])(C)(C)C.[ClH:28].O1CCOCC1>>[ClH:28].[NH2:7][CH:8]([C:10]1[S:11][CH:12]=[C:13]([C:15]([N:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19][CH2:18]2)=[O:16])[N:14]=1)[CH3:9]

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86623713HCID 86623713, compound

Product 1

HCID 69208396HCID 69208396, compound

Procedure

A solution of tert-butyl(1-(4-(1,2,3,4-tetrahydroquinoline-1-carbonyl)thiazol-2-yl)ethyl)-carbamate (180 mg, 0.47 mmol) in 4N hydrogen chloride/dioxan (10 ml) was stirred in an ice/water bath and allowed to warm to room temperature. The mixture was concentrated and azeotroped with toluene twice, tetrachloromethane twice and dichloromethane once to afford 1-(2-(1-aminoethyl)thiazole-4-carbonyl)-1,2,3,4-tetrahydroquinoline hydrochloride. The yield was assumed to be quantitative and the material was used directly by taking up in dichloromethane (5 ml) and triethylamine (0.16 ml, 118 mg, 1.2 mmol). The resulting solution was cooled in an ice/water bath and to it was added 4-bromobenzenesulphonyl chloride (119 mg, 0.47 mmol). The mixture was allowed to warm to room temperature and stirred for 18 h. Evaporation and chromatography (50% EtOAc/50% hexanes) afforded 1-(2-(1-(4-bromobenzenesulphonylamino)ethyl)thiazole-4-carbonyl)-1,2,3,4-tetrahydroquinoline as a white solid (144 mg, 61%).

Workup

  1. concentrationThe mixture was concentrated
  2. customazeotroped with toluene twice

Sources & evidence

ORD record
ord-7d36a2b87cb548ff8c4eeb62f2ec1022
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

Loading…