Water → N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-7-[(Z)-N'-hydroxycarbamimidoyl]-1-benzothiophene-2-carboxamide;dihydrochloride

HRID 658222Notes

Reaction equation

HRID 658222 reaction equation
[ClH:1].[N:2]12[CH2:9][CH2:8][CH:5]([CH2:6][CH2:7]1)[C@@H:4]([NH:10][C:11]([C:13]1[S:14][C:15]3[C:21]([C:22]#[N:23])=[CH:20][CH:19]=[CH:18][C:16]=3[CH:17]=1)=[O:12])[CH2:3]2.Cl.[NH2:25][OH:26].C(=O)([O-])[O-].[K+].[K+].O>C(O)C>[ClH:1].[ClH:1].[NH2:23]/[C:22](=[N:25]\[OH:26])/[C:21]1[C:15]2[S:14][C:13]([C:11]([NH:10][C@@H:4]3[CH:5]4[CH2:6][CH2:7][N:2]([CH2:9][CH2:8]4)[CH2:3]3)=[O:12])=[CH:17][C:16]=2[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 68431784HCID 68431784, compound

Product 1

HCID 87452962N-[(3R)-1-azabicyclo[2.2.2]octan-3-yl]-7-[(Z)-N'-hydroxycarbamimidoyl]-1-benzothiophene-2-carboxamide;dihydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

120 mg (0.43 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-cyano-1-benzothiophene-2-carboxamide hydrochloride, 45.0 mg (0.65 mmol) of hydroxylamine hydrochloride and 119.2 mg (0.86 mmol) of potassium carbonate in 1.5 ml of an 8:1 mixture of water and ethanol are heated at 80° C. for 18 h. The mixture is purified by preparative HPLC. The product fractions are combined and concentrated, acetonitrile and 1N aqueous hydrochloric acid (3:1) are added and the mixture is then again concentrated and dried under high vacuum. 58 mg (30.3% of theory) of the title compound are obtained.

Workup

  1. customThe mixture is purified by preparative HPLC
  2. concentrationconcentrated
  3. additionacetonitrile and 1N aqueous hydrochloric acid (3:1) are added
  4. concentrationthe mixture is then again concentrated
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-9a0c6d9d0f754f1187b69885322671c3
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

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