Trifluoroacetic acid → HCID 46865697, compound

HRID 1187730Notes

Reaction equation

HRID 1187730 reaction equation
CC1(C)[O:6][CH2:5][C:4]2([CH2:11][CH2:10][N:9]([C:12]3[CH:17]=[C:16]([NH:18][C:19]4[CH:24]=[N:23][CH:22]=[CH:21][N:20]=4)[N:15]=[C:14]([NH:25][C@H:26]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH3:27])[CH:13]=3)[CH2:8][CH2:7]2)[O:3]1.CC1(C)OCC2(CCNCC2)O1.O1CCOCC1.FC(F)(F)C(O)=O>C(Cl)(Cl)Cl>[F:34][C:31]1[CH:30]=[CH:29][C:28]([C@@H:26]([NH:25][C:14]2[CH:13]=[C:12]([N:9]3[CH2:8][CH2:7][C:4]([CH2:5][OH:6])([OH:3])[CH2:11][CH2:10]3)[CH:17]=[C:16]([NH:18][C:19]3[CH:24]=[N:23][CH:22]=[CH:21][N:20]=3)[N:15]=2)[CH3:27])=[CH:33][CH:32]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 312751,4-DioxaneHCID 53399401HCID 53399401, compoundHCID 67007952HCID 67007952, compound

Product 1

HCID 46865697HCID 46865697, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(S)-4-(2,2-Dimethyl-1,3-dioxa-8-azaspiro[4.5]decan-8-yl)-N2-[1-(4-fluorophenyl)ethyl]-N6-(pyrazin-2-yl)pyridine-2,6-diamine was obtained by the same process as in Example using 2,2-dimethyl-1,3-dioxa-8-azaspiro[4.5]decane instead of (S)—N-(pyrrolidin-3-yl)acetamide, and using 1,4-dioxane as a reaction solvent. 46 mg of the obtained compound was dissolved in 1 mL of chloroform, and 0.5 ml of 50% trifluoroacetic acid aqueous solution was added at 0° C. thereto, and the mixture was stirred. The solvent was distilled off under reduced pressure, and then the obtained residue was purified by silica gel column chromatography to obtain 21 mg of the objective compound as brown powder.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f567095db873478baa252a04603ffa8d
Source dataset
uspto-grants-2014_03
Patent number
US08673891B2

Reaction notes

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