Acetic Acid → HCID 178491294, compound

HRID 518675Notes

Reaction equation

HRID 518675 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][C:22]3[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=3)[CH:17]=[CH:16][C:15]=2[N+:30]([O-])=O)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].CC(O)=O>CO.[Zn]>[NH2:30][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=2)=[CH:19][C:14]=1[NH:13][C@@H:10]1[CH2:11][CH2:12][C@H:7]([C:5]([NH:4][CH:1]([CH3:3])[CH3:2])=[O:6])[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 178491295HCID 178491295, compound

Product 1

HCID 178491294HCID 178491294, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a solution of cis-N-isopropyl-4-(5-(4-methoxybenzyloxy)-2-nitrophenylamino)cyclohexanecarboxamide (452 mg, 1.024 mmol) in MeOH (5 mL) was added AcOH (0.293 mL, 5.12 mmol) and zinc (669 mg, 10.24 mmol), and the resulting mixture was stirred at RT for 3 hours. The mixture was filtered through a pad of Celite® brand filter aid and evaporated to afford cis-4-(2-amino-5-(4-methoxybenzyloxy)phenylamino)-N-isopropylcyclohexanecarboxamide (400 mg).

Workup

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

Sources & evidence

ORD record
ord-489d35e1d59241028ef31f24a4b3dc84
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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