4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → HCID 178452471, compound

HRID 1520783Notes

Reaction equation

HRID 1520783 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([OH:8])=O)=[N:2]1.[NH2:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[O:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)=[CH:12][CH:11]=1.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>CO>[NH:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C@@H:16]3[O:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]3)=[CH:12][CH:11]=2)=[O:8])=[N:2]1

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 66705988(S)-Tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylateHCID 178524567HCID 178524567, compound

Product 1

HCID 178452471HCID 178452471, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

1H-Pyrazole-3-carboxylic acid (560 mg, 5 mmol) was dissolved in methanol (62 ml) and (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (1.39 g, 5 mmol) was added. The solution was cooled to 0° C. and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (1.8 g, 6.5 mmol) dissolved in 5 ml methanol was added drop-wise to the reaction mixture in 1 hour. The reaction mixture was stirred at 0° C. for two hours then overnight at room temperature. The solvent was evaporated, the residue was dissolved in dichloromethane and adsorbed on silicagel.

Workup

  1. additionwas added drop-wise to the reaction mixture in 1 hour
  2. customovernight
  3. customat room temperature
  4. customThe solvent was evaporated
  5. dissolutionthe residue was dissolved in dichloromethane

Sources & evidence

ORD record
ord-5a62c1f973de4c3aa1c0d1b3396b9133
Source dataset
uspto-grants-2015_07
Patent number
US09073911B2

Reaction notes

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