Water → N,N-dimethyl-1-(2-(3-((methylsulfonyl)methyl)phenyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanamine

HRID 63798Notes

Reaction equation

HRID 63798 reaction equation
CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[N:18]=[C:17]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:16]3=[CH:25][C:26]([CH2:28][N:29]([CH3:31])[CH3:30])=[CH:27][N:15]3[N:14]=2)[CH:8]=1)(=O)=O.[CH3:32][S:33]([O-:35])=[O:34].[Na+].O>CN1CCCC1=O>[CH3:31][N:29]([CH3:30])[CH2:28][C:26]1[CH:25]=[C:16]2[N:15]([CH:27]=1)[N:14]=[C:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][S:33]([CH3:32])(=[O:35])=[O:34])[CH:8]=1)[N:18]=[C:17]2[N:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 2733271Sodium methanesulfinateHCID 117988030HCID 117988030, compound

Product 1

HCID 72201093N,N-dimethyl-1-(2-(3-((methylsulfonyl)methyl)phenyl)-4-morpholinopyrrolo[2,1-f][1,2,4]triazin-6-yl)methanamineYield 28%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Compound 19 (45 mg, 0.1 mmol) and sodium methylsulfinate (41 mg, 0.4 mmol) were dissolved in 2 mL N-methylpyrrolidone. The mixture was under microwave irradiation for 30 minutes at 120° C. with the power of 100 watts. After completion of the reaction, the reaction mixture was poured into water, extracted for three times with ethyl acetate, and extracted for three times with dichloromethane. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to a small volume. The crude product was purified by a preparative plate (dichloromethane:methanol=6:1) to obtain 12 mg of white solid (28.0%). m.p. 143-144° C. 1H NMR (300 MHz, CDCl3): δ 8.32 (d, J=5.2 Hz, 1H), 8.29 (s, 1H), 7.63 (d, J=1.2 Hz, 1H), 7.50 (d, J=5.2 Hz, 2H), 6.78 (d, J=1.2 Hz, 1H), 4.34 (s, 2H), 4.11 (t, J=4.4 Hz, 4H), 3.88 (t, J=4.4 Hz, 4H), 3.66 (s, 2H), 2.78 (s, 3H), 2.36 (s, 6H). MS (EI) m/e (%): 429 (M+, 12).

Workup

  1. customThe mixture was under microwave irradiation for 30 minutes at 120° C. with the power of 100 watts
  2. customAfter completion of the reaction
  3. extractionextracted for three times with ethyl acetate
  4. extractionextracted for three times with dichloromethane
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationThe solvent was concentrated under reduced pressure to a small volume
  7. customThe crude product was purified by a preparative plate (dichloromethane:methanol=6:1)

Sources & evidence

ORD record
ord-2366236a36d94abc91175c5debdc09b4
Source dataset
uspto-grants-2016_09
Patent number
US09447101B2

Reaction notes

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