2,6-Lutidine → HCID 86708545, compound

HRID 921677Notes

Reaction equation

HRID 921677 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:17][CH2:16][N:15]3[C@H:10]([CH2:11][O:12][C:13]([CH3:19])([CH3:18])[CH2:14]3)[CH2:9]2)=[CH:6][C:5]([C:20]#[N:21])=[CH:4][C:3]=1[NH:22]C(=O)OC(C)(C)C.N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si](C)(C)C)(=O)=O>C(Cl)Cl>[NH2:22][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([N:8]2[CH2:17][CH2:16][N:15]3[C@H:10]([CH2:11][O:12][C:13]([CH3:19])([CH3:18])[CH2:14]3)[CH2:9]2)[C:2]=1[Cl:1])[C:20]#[N:21]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 86708546HCID 86708546, compound

Product 1

HCID 86708545HCID 86708545, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-tert-butyl (2-chloro-5-cyano-3-(3,3-dimethylhexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl)phenyl)carbamate (87 mg, 0.207 mmol) was taken up in DCM (2 mL) and cooled to 0° C. 2,6-Lutidine (0.072 mL, 0.620 mmol) was added, followed by dropwise addition of trimethylsilyl trifluoromethanesulfonate (0.112 mL, 0.620 mmol). The reaction was stirred at 0° C. for 30 min, then warmed to room temperature and stirred for 30 min. The solvent was removed in vacuo and the material was purified by flash column chromatography, eluting with 0-2% (2N NH3/MeOH)/DCM. (S)-3-amino-4-chloro-5-(3,3-dimethylhexahydropyrazino[2,1-c][1,4]oxazin-8(1H)-yl)benzonitrile (22 mg) was obtained as a yellow glass.

Workup

  1. temperaturewarmed to room temperature
  2. stirringstirred for 30 min
  3. customThe solvent was removed in vacuo
  4. customthe material was purified by flash column chromatography
  5. washeluting with 0-2% (2N NH3/MeOH)/DCM

Sources & evidence

ORD record
ord-d9742883cb2b467cb953d50b73ced897
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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