Sodium Hydroxide → HCID 178482421, compound

HRID 1922021Notes

Reaction equation

HRID 1922021 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][CH3:15])[N:3]=1.[NH2:16][C@H:17]1[CH2:22][CH2:21][C@H:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]1.[OH-].[Na+]>CC#N.O.O>[CH3:15][NH:14][C:4]1[N:5]=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=[C:2]([NH:16][C@H:17]2[CH2:22][CH2:21][C@H:20]([C:23]([OH:25])=[O:24])[CH2:19][CH2:18]2)[N:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 16082HCID 16082, compoundHCID 178511567HCID 178511567, compound

Product 1

HCID 178482421HCID 178482421, compoundYield 20.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18373917Acetonitrile--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 4-chloro-N-methyl-6-phenyl-1,3,5-triazin-2-amine (1.0 g, 4.5 mmol) in CH3CN:H2O (1:1, 5 mL) was added trans-4-aminocyclohexanecarboxylic acid (973 mgs, 6.80 mmol). The solution was treated with 1 N NaOH to maintain a pH of 9-10 and stirred at 80° C. for 36 h. The resulting mixture was diluted with water and filtered to provide the crude product, which was purified by HPLC to afford 300 mg (20% yield) of the desired product. MS (ES+): m/e 328.2 [M+H]+.

Workup

  1. temperatureto maintain a pH of 9-10
  2. filtrationfiltered
  3. customto provide the crude product, which
  4. customwas purified by HPLC

Sources & evidence

ORD record
ord-7e862ba3d1474a7fb7ec1f69207eaeed
Source dataset
uspto-grants-2012_05
Patent number
US08173805B2

Reaction notes

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