Water → HCID 178461224, compound

HRID 81102Notes

Reaction equation

HRID 81102 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]([CH2:38][C@H:39]4[CH2:44][CH2:43][C@H:42]([CH3:45])[CH2:41][CH2:40]4)[C:24]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][C@H:27]4[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:25][C:21]=3[CH:20]=[C:19]([C:46]#[N:47])[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]([CH2:38][C@H:39]4[CH2:44][CH2:43][C@H:42]([CH3:45])[CH2:41][CH2:40]4)[C:24]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][C@H:27]4[C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)=[N:25][C:21]=3[CH:20]=[C:19]([C:46](=[N:2][OH:3])[NH2:47])[N:18]=2)[CH:14]=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 178461221HCID 178461221, compound

Product 1

HCID 178461224HCID 178461224, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Hydroxylamine hydrochloride (5.4 mg, 0.08 mmol), sodium bicarbonate (9.9 mg, 0.12 mmol), and water (0.12 mL) were combined in a vial and stirred for 15 minutes. This solution was added to a vial containing 4-(5-chloropyridin-3-yl)-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (20.6 mg, 0.04 mmol) dissolved in ethanol (0.3 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)-N′-hydroxy-3-[(trans-4-methylcyclohexyl)methyl]-2-[(3R)-3-phenylmorpholin-4-yl]-3H-imidazo[4,5-c]pyridine-6-carboximidamide. MS ESI calc'd. for C30H34ClN7O2 [M+H]+ 560. found 560.

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-fed2f6eaba774dc68d3289bfcc199d17
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

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