Hydroxyamine hydrochloride → HCID 178426679, compound

HRID 1711159Notes

Reaction equation

HRID 1711159 reaction equation
[C:1]([C:3]1[CH:28]=[C:27]([CH3:29])[C:6]([C:7]([NH:9][CH2:10][CH2:11][C@H:12]([N:14]2[CH2:19][CH2:18][CH:17]([NH:20][CH2:21][C:22]3[CH:26]=[CH:25][S:24][CH:23]=3)[CH2:16][CH2:15]2)[CH3:13])=[O:8])=[C:5]([CH3:30])[N:4]=1)#[N:2].Cl.[NH2:32][OH:33]>CCO.C(Cl)Cl.O.C([O-])(O)=O.[Na+]>[OH:33][NH:32][C:1]([C:3]1[CH:28]=[C:27]([CH3:29])[C:6]([C:7]([NH:9][CH2:10][CH2:11][C@H:12]([N:14]2[CH2:19][CH2:18][CH:17]([NH:20][CH2:21][C:22]3[CH:26]=[CH:25][S:24][CH:23]=3)[CH2:16][CH2:15]2)[CH3:13])=[O:8])=[C:5]([CH3:30])[N:4]=1)=[NH:2]

Participants

7

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 68776907HCID 68776907, compound

Product 1

HCID 178426679HCID 178426679, compoundYield 77%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent2×

Procedure

To a solution of 6-cyano-2,4-dimethyl-N—((R)-3-{4-[(thiophen-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-nicotinamide (208 mg, 0.49 mmol) in EtOH (3 ml) was added hydroxylamine HCl (190 mg, 2.73 mmol) and NaHCO3 (239 mg, 2.84 mmol) and the reaction heated to reflux overnight. The mixture was diluted with CH2Cl2 (25 ml) and water (10 ml) and saturated aqueous NaHCO3 (20 ml). The aqueous layer was extracted with CH2Cl2 (2×5 ml) and the combined organic extracts were dried (Na2SO4) and concentrated to afford 6-(N-hydroxycarbamimidoyl)-2,4-dimethyl-N—((R)-3-{4-[(thiophen-3-ylmethyl)-amino]-piperidin-1-yl}-butyl)-nicotinamide (173 mg) as a beige foam.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux overnight
  3. extractionThe aqueous layer was extracted with CH2Cl2 (2×5 ml)
  4. dry with materialthe combined organic extracts were dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-861530fc56fe4f6281c01086394e884d
Source dataset
uspto-grants-2010_09
Patent number
US07790747B2

Reaction notes

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