Ammonium trifluoroacetate → 4-methoxy-2-[5-(3-methyl-benzo[b]thiophen-2-yl)-1H-imidazol-2-yl]-7-morpholin-4-yl-benzothiazole

HRID 1244342Notes

Reaction equation

HRID 1244342 reaction equation
[CH3:1][C:2]1[C:3]2[CH:33]=[CH:32][CH:31]=[CH:30][C:4]=2[S:5][C:6]=1[C:7](=O)[CH2:8][NH:9][C:10]([C:12]1[S:13][C:14]2[C:20]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:19][CH:18]=[C:17]([O:27][CH3:28])[C:15]=2[N:16]=1)=O.FC(F)(F)C([O-])=O.[NH4+:41]>O>[CH3:28][O:27][C:17]1[C:15]2[N:16]=[C:12]([C:10]3[NH:41][C:7]([C:6]4[S:5][C:4]5[CH:30]=[CH:31][CH:32]=[CH:33][C:3]=5[C:2]=4[CH3:1])=[CH:8][N:9]=3)[S:13][C:14]=2[C:20]([N:21]2[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 2724268Ammonium trifluoroacetateHCID 211370764-Methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid [2-(3-methyl-benzo[b]thiophen-2-yl)-2-oxo-ethyl]-amide

Product 1

HCID 219192124-methoxy-2-[5-(3-methyl-benzo[b]thiophen-2-yl)-1H-imidazol-2-yl]-7-morpholin-4-yl-benzothiazoleYield 52.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.16 g 4-methoxy-7-morpholin-4-yl-benzothiazole-2-carboxylic acid [2-(3-methyl-benzo[b]thiophen-2-yl)-2-oxo-ethyl]-amide and 0.44 g ammonium triflouroacetate was melted at 180° C. for 45 minutes and, after cooling to room temperature, suspended in water. Extraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 1:1 gave 0.08 g (51%) 4-methoxy-2-[5-(3-methyl-benzo[b]thiophen-2-yl)-1H-imidazol-2-yl]-7-morpholin-4-yl-benzothiazole as yellow solid; M.p.: 213–215° C.; MS (ISP): m/e=463 (M+H+).

Workup

  1. customfor 45 minutes
  2. extractionExtraction with dichloromethane and chromatography on silicagel with ethylacetate/hexane 1:1

Sources & evidence

ORD record
ord-84a449fad0d0452989f4eaf1bc19a57f
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

Loading…