Diisopropylethylamine → HCID 86633864, compound

HRID 1040716Notes

Reaction equation

HRID 1040716 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([Cl:8])=[C:4](Cl)[N:3]=1.[CH3:10][NH:11][C:12]([C@@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]1[NH2:20])=[O:13].C(N(CC)C(C)C)(C)C>C(O)(C)C>[CH3:10][NH:11][C:12]([C@@H:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C@@H:15]1[NH:20][C:4]1[C:5]([Cl:8])=[CH:6][N:7]=[C:2]([Cl:1])[N:3]=1)=[O:13]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2372592,4,5-TrichloropyrimidineHCID 13697511HCID 13697511, compound

Product 1

HCID 86633864HCID 86633864, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

2,5,6-trichloropyrimidine (368 mg, 2.0 mmol), cis-2-amino-cyclohexanecarboxylic acid methylamide (308 mg, 2.0 mmol), and N,N-diisopropylethylamine (387 mg, 3.0 mmol) were combined in 10 mL isopropyl alcohol and stirred at room temperature for 24 hours. The reaction was concentrated and the organics were partitioned between dichloromethane and saturated sodium bicarbonate solution (100 mL each). The organic layer was separated and was dried (sodium sulfate) to afford a solid which was purified on silica gel (1% to 3% methanol:dichloromethane gradient elution) to afford 502 mg (83%) of cis-2-(2,5-dichloro-pyrimidin-4-ylamino)-cyclohexanecarboxylic acid methylamide as a white foam. Mp: 108° C.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe organics were partitioned between dichloromethane and saturated sodium bicarbonate solution (100 mL each)
  3. customThe organic layer was separated
  4. dry with materialwas dried (sodium sulfate)
  5. customto afford a solid which
  6. customwas purified on silica gel (1% to 3% methanol:dichloromethane gradient elution)

Sources & evidence

ORD record
ord-f58457d27cae463bb783566e7f50d254
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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