Water → HCID 178496637, compound

HRID 81180Notes

Reaction equation

HRID 81180 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]([CH2:36][C@H:37]4[CH2:42][CH2:41][C@H:40]([CH3:43])[CH2:39][CH2:38]4)[C:24]([N:26]4[CH2:30][C@H:29]([O:31][CH3:32])[CH2:28][C@H:27]4[CH:33]([CH3:35])[CH3:34])=[N:25][C:21]=3[CH:20]=[C:19]([C:44]#[N:45])[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]([CH2:36][C@H:37]4[CH2:38][CH2:39][C@H:40]([CH3:43])[CH2:41][CH2:42]4)[C:24]([N:26]4[CH2:30][C@H:29]([O:31][CH3:32])[CH2:28][C@H:27]4[CH:33]([CH3:35])[CH3:34])=[N:25][C:21]=3[CH:20]=[C:19]([C:44](=[N:2][OH:3])[NH2:45])[N:18]=2)[CH:14]=[N:15][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 516892Sodium BicarbonateHCID 178496636HCID 178496636, compound

Product 1

HCID 178496637HCID 178496637, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

Hydroxylamine hydrochloride (20.2 mg, 0.29 mmol), sodium bicarbonate (36.6 mg, 0.44 mmol), and water (0.436 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,4R)-4-methoxy-2-(propan-2-yl)pyrrolidin-1-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carbonitrile (73.7 mg, 0.145 mmol) dissolved in ethanol (1 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-2-[(2S,4R)-4-methoxy-2-(propan-2-yl)pyrrolidin-1-yl]-3-[(trans-4-methylcyclohexyl)methyl]-3H-imidazo[4,5-c]pyridine-6-carboximidamide. MS ESI calc'd. for C28H38ClN7O2 [M+H]+ 540. found 540.

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-76740bb418544052b0faeb6f6dea67d7
Source dataset
uspto-grants-2014_09
Patent number
US08846657B2

Reaction notes

Loading…