Ammonium Hydroxide → HCID 178458677, compound

HRID 518760Notes

Reaction equation

HRID 518760 reaction equation
[OH:1][C:2]([CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([N+:28]([O-:30])=[O:29])=[C:16]([NH:18][C@H:19]3[CH2:24][CH2:23][C@H:22]([C:25]([OH:27])=O)[CH2:21][CH2:20]3)[CH:17]=2)[CH2:7][CH2:6]1)([CH3:4])[CH3:3].C1N=C[N:33](C(N2C=NC=C2)=O)C=1.[OH-].[NH4+]>CN(C=O)C>[OH:1][C:2]([CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([N+:28]([O-:30])=[O:29])=[C:16]([NH:18][C@H:19]3[CH2:20][CH2:21][C@H:22]([C:25]([NH2:33])=[O:27])[CH2:23][CH2:24]3)[CH:17]=2)[CH2:9][CH2:10]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 178458679HCID 178458679, compound

Product 1

HCID 178458677HCID 178458677, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of trans-4-(5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)cyclohexanecarboxylic acid (0.53 g, 1.263 mmol) in DMF (5 mL) was added CDI (0.410 g, 2.53 mmol). The reaction was stirred at RT for 1 hour, and then concentrated aqueous ammonium hydroxide (0.098 mL, 2.53 mmol) was added, and the reaction was stirred overnight. After 16 hours, the reaction mixture was partitioned between water and EtOAc. The aqueous layer was extracted with EtOAc, and the combined organic layers were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography, eluting with 50-100% (90:9:1 DCM/MeOH/NH4OH)/DCM, to provide trans-4-(5-((4-(2-hydroxypropan-2-yl)piperidin-1-yl)methyl)-2-nitrophenylamino)cyclohexanecarboxamide as an orange powder (0.39 g, 73.8% yield). MS, m/z (C22H34FN4O4): calcd, 418.3. found, 419.1 [M+H].

Workup

  1. stirringthe reaction was stirred overnight
  2. waitAfter 16 hours
  3. customthe reaction mixture was partitioned between water and EtOAc
  4. extractionThe aqueous layer was extracted with EtOAc
  5. washthe combined organic layers were washed with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography
  10. washeluting with 50-100% (90:9:1 DCM/MeOH/NH4OH)/DCM

Sources & evidence

ORD record
ord-b2bff4ec609f48e6b766a9e76cd8da42
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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