(R)-1,2-Epoxypropane → HCID 56945611, compound

HRID 1262125Notes

Reaction equation

HRID 1262125 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([CH:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)=[CH:21][C:20]=3[O:31][CH3:32])=[N:16]2)=[CH:11][CH:10]=1.[CH2:33]1[O:36][C@@H:34]1[CH3:35]>O1CCCC1>[CH3:32][O:31][C:20]1[CH:21]=[C:22]([CH:25]2[CH2:30][CH2:29][N:28]([CH2:33][C@H:34]([OH:36])[CH3:35])[CH2:27][CH2:26]2)[CH:23]=[CH:24][C:19]=1[NH:18][C:15]1[N:14]=[CH:13][C:12]2=[CH:11][CH:10]=[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])[N:17]2[N:16]=1

Participants

4

Reactant 2

HCID 146261(R)-1,2-EpoxypropaneHCID 66711490HCID 66711490, compound

Product 1

HCID 56945611HCID 56945611, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(2-methoxy-4-piperidin-4-yl-phenyl)-amine (70.00 mg, 0.163 mmol) was dissolved in tetrahydrofuran (0.300 mL) and the reaction mixture was placed in a sealed tube. (R)-(−)-Propylene oxide (14.2 mg, 0.244 mmol) was then added at room temperature and the reaction was next stirred overnight at 50° C. The solvent was evaporated under reduced pressure and the product was isolated by flash column chromatography (Silicagel, methanol/dichloromethane 0-10% gradient) to afford (R)-1-(4-{3-methoxy-4-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-phenyl}-piperidin-1-yl)-propan-2-ol as a tan solid (39 mg, 49%). MP: 67-74° C.; 1H-NMR (CDCl3) δ 8.69 (s, 1H), 8.29 (d, J=8.1 Hz, 1H), 7.99 (d, J=7.7 Hz, 1H), 7.43 (m, 2H), 7.14 (m, 1H), 7.07 (d, J=8.4 Hz, 1H), 7.02 (d, J=4.4 Hz, 1H), 6.83 (d, J=4.4 Hz, 1H), 6.73 (s, 1H), 6.71 (d, J=8.1 Hz, 1H), 3.90 (s, 3H), 3.89 (m, 1H), 3.84 (s, 3H), 3.15 (m, 1H), 2.94 (m, 1H), 2.35 (m, 4H), 2.06 (m, 1H), 1.79 (m, 4H), 1.30 (br s, 1H), 1.16 (d, J=5.8 Hz, 3H); LC/MS (ESI+): 488.2 (M+H).

Workup

  1. customthe reaction mixture was placed in a sealed tube
  2. customThe solvent was evaporated under reduced pressure
  3. customthe product was isolated by flash column chromatography (Silicagel, methanol/dichloromethane 0-10% gradient)

Sources & evidence

ORD record
ord-3635fbc990be4671a64af04d9ed2ef0d
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

Loading…