Hydrochloric Acid → N-[2-[4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl]ethyl]-2-[3-[2-[4-fluorophenyl]ethoxy]propylsulphonyl]acetamide

HRID 265306Notes

Reaction equation

HRID 265306 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[F:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][O:22][CH2:23][CH2:24][CH2:25][S:26]([CH2:29][C:30]([OH:32])=O)(=[O:28])=[O:27])=[CH:16][CH:15]=1.Br.[NH2:34][CH2:35][CH2:36][C:37]1[C:45]2[S:44][C:43](=[O:46])[NH:42][C:41]=2[C:40]([OH:47])=[CH:39][CH:38]=1.Cl>CN(C=O)C.CCOCC.C(N(CC)CC)C>[OH:47][C:40]1[C:41]2[NH:42][C:43](=[O:46])[S:44][C:45]=2[C:37]([CH2:36][CH2:35][NH:34][C:30](=[O:32])[CH2:29][S:26]([CH2:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=2)(=[O:27])=[O:28])=[CH:38][CH:39]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 138142707-(2-Aminoethyl)-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromideHCID 190342082-[3-[2-[4-Fluorophenyl]ethoxy]propylsulphonyl]acetic acid

Product 1

HCID 19082282N-[2-[4-Hydroxy-2-oxo-3H-1,3-benzothiazol-7-yl]ethyl]-2-[3-[2-[4-fluorophenyl]ethoxy]propylsulphonyl]acetamide

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

Carbonyl diimidazole (1.94 g) was added to a stirred solution of the acid from step c) (3.64 g) in DMF (15 ml). Stirring was continued for 40 min at room temperature. To this solution was added 7-[2-aminoethyl]-4-hydroxy-1,3-benzothiazol-2(3H)-one hydrobromide (3.48 g) followed by triethylamine (1.7 ml). The whole was left overnight. The reaction mixture was then added slowly to a rapidly stirred mixture of 10% aqueous hydrochloric acid and ether (100 ml each). A pale yellow solid gradually settled out and was filtered off, washed with pentane and dried in vacuo. This provided the subtitled compound as a buff coloured material which was used in the next step without further purification.

Workup

  1. waitThe whole was left overnight
  2. filtrationwas filtered off
  3. washwashed with pentane
  4. customdried in vacuo

Sources & evidence

ORD record
ord-ef65cc57763e4535b5b46c82ac0e0166
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

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