4-Isocyanato-1-(trifluoroacetyl)piperidine → HCID 66915784, compound

HRID 2356961Notes

Reaction equation

HRID 2356961 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[C:13]([CH3:15])([CH3:14])[C:12](=[O:16])[N:11]([C:17]3[CH:25]=[C:24]4[C:20]([C:21]([CH3:27])([CH3:26])[CH2:22][NH:23]4)=[CH:19][CH:18]=3)[C:10]2=[O:28])[CH:5]=[CH:4][N:3]=1.[N:29]([CH:32]1[CH2:37][CH2:36][N:35](C(=O)C(F)(F)F)[CH2:34][CH2:33]1)=[C:30]=[O:31]>C1COCC1>[NH:35]1[CH2:36][CH2:37][CH:32]([NH:29][C:30]([N:23]2[C:24]3[C:20](=[CH:19][CH:18]=[C:17]([N:11]4[C:12](=[O:16])[C:13]([CH3:15])([CH3:14])[N:9]([CH2:8][C:6]5[CH:5]=[CH:4][N:3]=[C:2]([NH2:1])[N:7]=5)[C:10]4=[O:28])[CH:25]=3)[C:21]([CH3:27])([CH3:26])[CH2:22]2)=[O:31])[CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 27789674-Isocyanato-1-(trifluoroacetyl)piperidineHCID 66915758HCID 66915758, compound

Product 1

HCID 66915784HCID 66915784, compoundYield 22.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

200 mg (0.53 mmol) of 1-(2-aminopyrimidin-4-ylmethyl)-3-(3,3-dimethyl-2,3-dihydro-1H-indol-6-yl)-5,5-dimethylimidazolidine-2,4-dione were dissolved in 3 ml of THF, and a solution of 118 mg (0.53 mmol) of 4-isocyanatotrifluoroacetylpiperidine in 3 ml of THF was added. After stirring at RT for 1 h, the mixture is concentrated and taken up in 3 ml of dioxane and 3 ml of 2 N HCl, and the mixture is heated in a microwave at 120° C. for 15 min. For workup, the mixture was concentrated and the remaining residue was purified by means of preparative HPLC (RP18, acetonitrile/water, 0.1% TFA). After release of the base by treating with sodium hydrogencarbonate solution, 60 mg of the title compound were obtained.

Workup

  1. concentrationthe mixture is concentrated
  2. temperature3 ml of 2 N HCl, and the mixture is heated in a microwave at 120° C. for 15 min
  3. concentrationFor workup, the mixture was concentrated
  4. customthe remaining residue was purified by means of preparative HPLC (RP18, acetonitrile/water, 0.1% TFA)
  5. additionAfter release of the base by treating with sodium hydrogencarbonate solution

Sources & evidence

ORD record
ord-9edd824d2da941bcb99e2256b824887e
Source dataset
uspto-grants-2010_07
Patent number
US07759379B2

Reaction notes

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