Triethylamine → 5-chloro-N'-hydroxy-1-(4-methylphenyl)sulfonyl-2-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridine-4-carboximidamide

HRID 2362738Notes

Reaction equation

HRID 2362738 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:19])=[O:18])[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:10][C:4]=2[C:3]=1[C:27]#[N:28].Cl.[NH2:30][OH:31].C(N(CC)CC)C>C(O)C.O>[Cl:1][C:2]1[CH:7]=[N:6][C:5]2[N:8]([S:17]([C:20]3[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=3)(=[O:18])=[O:19])[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)=[CH:10][C:4]=2[C:3]=1/[C:27](=[N:30]/[OH:31])/[NH2:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 443297Hydroxyamine hydrochloride2×HCID 670035475-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile2×

Product 1

HCID 1363794975-chloro-N'-hydroxy-1-(4-methylphenyl)sulfonyl-2-(1-methylpyrazol-4-yl)pyrrolo[2,3-b]pyridine-4-carboximidamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 5-chloro-2-(1-methyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-carbonitrile (Example 138A (160 mg, 0.388 mmol)) in ethanol (4 mL) and water (0.33 mL) was treated with hydroxylamine hydrochloride (54.0 mg, 0.777 mmol) and triethylamine (0.271 mL, 1.942 mmol). The reaction vessel was sealed, and the reaction mixture was heated for 30 minutes at 80° C. Additional hydroxylamine hydrochloride (10.0 mg, 0.143 mmol) added, and the reaction heated for 1 hour at 80° C. The reaction was cooled, diluted with water, and extracted with dichloromethane. The combined organics were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluting with a gradient of 50 to 70% ethyl acetate in hexanes, to provide the title compound. MS ESI(+) m/z 445.4 [M+H]+.

Workup

  1. customThe reaction vessel was sealed
  2. temperaturethe reaction heated for 1 hour at 80° C
  3. temperatureThe reaction was cooled
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash chromatography on silica gel
  9. washeluting with a gradient of 50 to 70% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-ae3ebf1072b24ca6be8c6dbf3e5e1d3b
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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