Water → HCID 178461211, compound

HRID 1852778Notes

Reaction equation

HRID 1852778 reaction equation
Cl.[NH2:2][OH:3].C(=O)(O)[O-].[Na+].O.[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[C:22]3[N:23]([CH2:33][C@H:34]4[CH2:39][CH2:38][C@H:37]([CH3:40])[CH2:36][CH2:35]4)[C:24]([N:26]4[CH2:30][CH2:29][CH2:28][C@H:27]4[CH2:31][F:32])=[N:25][C:21]=3[CH:20]=[C:19]([C:41]#[N:42])[N:18]=2)[CH:14]=[N:15][CH:16]=1>C(O)C>[Cl:10][C:11]1[CH:12]=[C:13]([C:17]2[C:22]3[N:23]([CH2:33][C@H:34]4[CH2:39][CH2:38][C@H:37]([CH3:40])[CH2:36][CH2:35]4)[C:24]([N:26]4[CH2:30][CH2:29][CH2:28][C@H:27]4[CH2:31][F:32])=[N:25][C:21]=3[CH:20]=[C:19]([C:41](=[N:2][OH:3])[NH2:42])[N:18]=2)[CH:14]=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 178461210HCID 178461210, compound

Product 1

HCID 178461211HCID 178461211, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Hydroxylamine hydrochloride (108 mg, 1.56 mmol), sodium bicarbonate (196 mg, 2.34 mmol), and water (1.56 mL) were combined in a vial and stirred for 15 minutes. This solution was added to a vial containing 4-(5-chloropyridin-3-yl)-2-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (364 mg, 0.78 mmol) dissolved in ethanol (3.6 mL). The mixture was sealed and heated at 100° C. for 1 hour. The reaction was cooled to room temperature, quenched with water, and extracted with ethyl acetate (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to afford 4-(5-chloropyridin-3-yl)-2-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]-N′-hydroxy-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carboximidamide. MS ESI calc'd. for C25H31ClFN7O [M+H]+ 500. found 500.

Workup

  1. additionThis solution was added to
  2. customThe mixture was sealed
  3. temperatureThe reaction was cooled to room temperature
  4. customquenched with water
  5. extractionextracted with ethyl acetate (2×)
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-8f5141b93f044cd890c9b1268915d2d0
Source dataset
uspto-grants-2015_02
Patent number
US08962611B2

Reaction notes

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