Sodium Iodide → 2-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl]-acetamide

HRID 1244384Notes

Reaction equation

HRID 1244384 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[NH:22][C:16]4[CH2:17][CH2:18][NH:19][CH2:20][CH2:21][C:15]=4[N:14]=3)[S:12][C:8]=2[C:7]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[CH:6][CH:5]=1.Br[CH2:30][C:31]([NH2:33])=[O:32].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>C(#N)C>[CH3:2][O:3][C:4]1[C:9]2[N:10]=[C:11]([C:13]3[NH:22][C:16]4[CH2:17][CH2:18][N:19]([CH2:30][C:31]([NH2:33])=[O:32])[CH2:20][CH2:21][C:15]=4[N:14]=3)[S:12][C:8]=2[C:7]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 696322-BromoacetamideHCID 114415902-(4-Methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine hydrochloride

Product 1

HCID 219192372-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl]-acetamideYield 27,508%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 0.04 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-1,4,5,6,7,8-hexahydro-imidazo[4,5-d]azepine hydrochloride in 5 ml acetonitrile were added 0.017 mg 2-bromoacetamide, 0.026 mg sodium carbonate and 0.018 mg sodium iodide. The mixture was refluxed for 17 hours, silicagel was added and the solvent was distilled off. The residue was transferred to a column prefilled with silicagel and was chromatographed with dichloromethane/methanol 95:5. Product containing fractions were further purified by chromatography on aluminium oxide with dichloromethane/methanol 95:5 to 4:1 to yield 0.015 g (34%) 2-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-4,5,7,8-tetrahydro-1H-imidazo[4,5-d]azepin-6-yl]-acetamide as yellow solid; M.p.: 299–302° C.; MS (ISP): m/e 443 (M+H+).

Workup

  1. temperatureThe mixture was refluxed for 17 hours
  2. additionsilicagel was added
  3. distillationthe solvent was distilled off
  4. customwas chromatographed with dichloromethane/methanol 95:5
  5. additionProduct containing fractions
  6. customwere further purified by chromatography on aluminium oxide with dichloromethane/methanol 95:5 to 4:1

Sources & evidence

ORD record
ord-de9926a6d599409aaaf941381b876b71
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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