Triethylamine → N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-(2-furoylamino)-1-benzothiophene-2-carboxamide hydrochloride

HRID 15478

Reaction equation

HRID 15478 reaction equation
Cl.Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[C@@H:5]([NH:11][C:12]([C:14]1[S:15][C:16]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][C:17]=3[CH:18]=1)=[O:13])[CH2:4]2.C(N(CC)CC)C.[O:31]1[CH:35]=[CH:34][CH:33]=[C:32]1[C:36]([Cl:38])=[O:37]>CN(C=O)C>[ClH:38].[N:3]12[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10]1)[C@@H:5]([NH:11][C:12]([C:14]1[S:15][C:16]3[CH:22]=[CH:21][C:20]([NH:23][C:36]([C:32]4[O:31][CH:35]=[CH:34][CH:33]=4)=[O:37])=[CH:19][C:17]=3[CH:18]=1)=[O:13])[CH2:4]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682422-Furancarbonyl chlorideHCID 68431067N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzothiophene-2-carboxamide dihydrochloride

Product 1

HCID 68432467N-[(3R)-1-Azabicyclo[2.2.2]oct-3-yl]-5-(2-furoylamino)-1-benzothiophene-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

30 mg (0.08 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-5-amino-1-benzo-thiophene-2-carboxamide dihydrochloride are dissolved in 1 ml of DMF, and 33.5 μl (0.24 mmol) of triethylamine are added. At 0° C., 15.7 mg (0.12 mmol) of furan-2-carbonyl chloride are added. After 3 h of stirring at RT, the reaction mixture is separated by preparative HPLC. The product fraction is concentrated under reduced pressure and codistilled with 4M HCl in dioxane. 12 mg (34.7% of theory) of the title compound are obtained.

Workup

  1. customthe reaction mixture is separated by preparative HPLC
  2. concentrationThe product fraction is concentrated under reduced pressure

Sources & evidence

ORD record
ord-a39e258bb5ad4d10ad19ecec143f5475
Source dataset
uspto-grants-2010_06
Patent number
US07732477B2

Linked notes

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