Phenyl isocyanate → 7-[(Anilinocarbonyl)amino]-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzothiophene-2-carboxamide hydrochloride

HRID 1691638Notes

Reaction equation

HRID 1691638 reaction equation
[ClH:1].Cl.[NH2:3][C:4]1[C:12]2[S:11][C:10]([C:13]([NH:15][C@@H:16]3[CH:21]4[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]4)[CH2:17]3)=[O:14])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1.C(N(CC)CC)C.[C:31]1([N:37]=[C:38]=[O:39])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C1COCC1>[ClH:1].[NH:37]([C:38]([NH:3][C:4]1[C:12]2[S:11][C:10]([C:13]([NH:15][C@@H:16]3[CH:21]4[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]4)[CH2:17]3)=[O:14])=[CH:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)=[O:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 669037637-amino-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzothiophene-2-carboxamide dihydrochloride

Product 1

HCID 669047427-[(Anilinocarbonyl)amino]-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzothiophene-2-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 44 mg (0.12 mmol) of 7-amino-N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-1-benzothiophene-2-carboxamide dihydrochloride in 2 ml of THF is mixed with 32.8 μl (0.24 mmol) of triethylamine and 28 mg (0.24 mmol) of phenyl isocyanate. After 18 h at room temperature, the product is purified by preparative HPLC. The concentrated product fraction is dissolved in a mixture of acetonitrile and 1 N hydrochloric acid (5:1), again concentrated and dried under high vacuum. 20 mg (36.1% of theory) of the title compound are obtained.

Workup

  1. customthe product is purified by preparative HPLC
  2. dissolutionThe concentrated product fraction is dissolved in a mixture of acetonitrile and 1 N hydrochloric acid (5:1)
  3. concentrationagain concentrated
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-06652cd54b8c409ebec0df48071c6a92
Source dataset
uspto-grants-2012_04
Patent number
US08153799B2

Reaction notes

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