Hydrochloric Acid → n-(5-Chloropyridin-2-yl)-2-[4-isopropyl-2-(4-oxocyclohexyloxy)-benzoylamino]benzamide

HRID 644215Notes

Reaction equation

HRID 644215 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:38])[C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][C:19]=2[O:27][CH:28]2[CH2:37][CH2:36][C:31]3(OCC[O:32]3)[CH2:30][CH2:29]2)=[N:6][CH:7]=1.Cl.O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:39])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17](=[O:38])[C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][C:19]=2[O:27][CH:28]2[CH2:37][CH2:36][C:31](=[O:32])[CH2:30][CH2:29]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 68535594N-(5-Chloropyridin-2-yl)-2-[2-(1,4-dioxaspiro[4.5]dec-8-yloxy)-4-isopropyl-benzoylamino]benzamide

Product 1

HCID 57860916n-(5-Chloropyridin-2-yl)-2-[4-isopropyl-2-(4-oxocyclohexyloxy)-benzoylamino]benzamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(5-Chloropyridin-2-yl)-2-[2-(1,4-dioxaspiro[4.5]dec-8-yloxy)-4-isopropyl-benzoylamino]benzamide (960 mg, 1.75 mmol) was dissolved in THF (30 mL). The solution was cooled to ice-water bath temperature and 5 M HCl (5.6 mL, 28 mmol) was added dropwise. The reaction was allowed to warm to room temperature and stir for 6 h. Water (100 mL) was added, and the pH was adjusted to 8 with 5 M NaOH. THF was removed on the rotary evaporator and the precipitated white solid was filtered, washed with water, and dried under vacuum to give 790 mg (90%) of the desired ketone as a white solid.

Workup

  1. additionwas added dropwise
  2. customTHF was removed on the rotary evaporator
  3. filtrationthe precipitated white solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-fb6f185e951347fe8d134bf04c25c143
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

Loading…