Diisopropylethylamine → HCID 178457831, compound

HRID 518644

Reaction equation

HRID 518644 reaction equation
Cl.[NH2:2][C@@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.CCN(C(C)C)C(C)C.[Cl:24][C:25]1[CH:30]=[C:29](Cl)[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1>C(#N)C.O>[Cl:24][C:25]1[CH:30]=[C:29]([NH:2][C@@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([NH:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH2:7][CH2:8]2)[C:28]([N+:32]([O-:34])=[O:33])=[CH:27][N:26]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 122757652,4-Dichloro-5-nitropyridineHCID 178457872HCID 178457872, compound

Product 1

HCID 178457831HCID 178457831, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of cis-4-amino-N-isopropylcyclohexanecarboxamide hydrochloride (12.58 g, 57.0 mmol) and DIPEA (29.0 mL, 166 mmol) in ACN (104 mL) was added 2,4-dichloro-5-nitropyridine (10.00 g, 51.8 mmol). The resulting mixture was stirred at RT for 24 hours. The reaction mixture was diluted with water and washed with DCM (×2). The combined organic layers were washed with a minimal volume of brine, dried over sodium sulfate, filtered and concentrated in vacuo. After almost complete concentration of solvent, EtOAc was added, and the solid precipitate was collected yielding cis-4-(2-chloro-5-nitropyridin-4-ylamino)-N-isopropylcyclohexanecarboxamide as a yellow solid (12.97 g, 73.4% yield).

Workup

  1. washwashed with DCM (×2)
  2. washThe combined organic layers were washed with a minimal volume of brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. concentrationAfter almost complete concentration of solvent, EtOAc
  7. additionwas added
  8. customthe solid precipitate was collected

Sources & evidence

ORD record
ord-a2f0400b1f944df0b7ffa6e47a56d027
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Linked notes

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