Acetic Acid → HCID 178457855, compound

HRID 518682Notes

Reaction equation

HRID 518682 reaction equation
[CH:1]([NH:4][C:5]([C@H:7]1[CH2:12][CH2:11][C@@H:10]([NH:13][C:14]2[CH:19]=[C:18]([O:20][CH2:21][CH2:22][N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:17]=[CH:16][C:15]=2[N+:29]([O-])=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].CC(O)=O>CO.[Zn]>[NH2:29][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH2:21][CH2:22][N:23]2[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]2)=[CH:19][C:14]=1[NH:13][C@@H:10]1[CH2:9][CH2:8][C@H:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:12][CH2:11]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178457856HCID 178457856, compound

Product 1

HCID 178457855HCID 178457855, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of cis-N-isopropyl-4-(2-nitro-5-(2-(piperidin-1-yl)ethoxy)phenylamino)cyclohexanecarboxamide (350 mg, 0.809 mmol) in MeOH (4.0 mL) was added AcOH (0.463 mL, 8.09 mmol) and zinc (423 mg, 6.47 mmol), and the mixture was stirred at RT for 1 hour. The mixture was filtered through a pad of Celite® brand filter aid and evaporated to afford cis-4-(2-amino-5-(2-(piperidin-1-yl)ethoxy)phenylamino)-N-isopropylcyclohexanecarboxamide.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite® brand
  2. filtrationfilter aid
  3. customevaporated

Sources & evidence

ORD record
ord-5c228a472f3b4019bfa2c9f3088ed8cf
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

Loading…