Hydroxylamine → HCID 136627687, compound

HRID 1254070Notes

Reaction equation

HRID 1254070 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:19]=[CH:18][N:17]([CH2:20][CH3:21])[N:16]=3)=[N:11][C:10]=2[C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[NH2:30][OH:31].CC(N(C)C)=O>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:19]=[CH:18][N:17]([CH2:20][CH3:21])[N:16]=3)=[N:11][C:10]=2[C:22]2[CH:23]=[CH:24][C:25]([C:26](=[N:30][OH:31])[NH2:27])=[CH:28][CH:29]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 31374DimethylacetamideHCID 58497198HCID 58497198, compound

Product 1

HCID 136627687HCID 136627687, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of step 3 product C-5 (240 mg, 0.572 mmol) in EtOH (5 ml) was added hydroxylamine (199 mg, 2.86 mmol) and DMA (0.498 ml, 2.86 mmol). After stirred at rt for 10 min, the reaction mixture was heated at 80° C. for 2 hrs. and then concentrated. To the residue was added EtOAc and washed with Na2CO3 (aq), organic layer was dried, and concentrated to give 4-{5-[(4-chlorophenyl)sulfanyl]-2-(1-ethyl-1H-pyrazol-3-yl)-1-methyl-1H-imidazol-4-yl}-N′-hydroxybenzenecarboximidamide (230 mg), which was used for further reaction without purification. LCMS: [M+1]+=453.2.

Workup

  1. temperaturethe reaction mixture was heated at 80° C. for 2 hrs
  2. concentrationand then concentrated
  3. additionTo the residue was added EtOAc
  4. washwashed with Na2CO3 (aq), organic layer
  5. customwas dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-fc4dc6a4fb0a4cd08cb0424a14070eaf
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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