HCID 90406336, compound → HCID 81689841, compound

HRID 2277043Notes

Reaction equation

HRID 2277043 reaction equation
[O:1]=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:7]=1)[CH2:3][C:4]#[N:5]>C1COCC1>[NH2:5][CH2:4][CH2:3][C@H:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:7]=1)[OH:1]

Participants

3

Reactant 1

HCID 90406336HCID 90406336, compound

Product 1

HCID 81689841HCID 81689841, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

BH3-Me2S (0.43 g, 5.8 mmol) was added dropwise to a solution of ketonitrile (13) (0.5 g, 1.9 mmol) in THF (50 mL). The reaction mixture was heated at 65° C. under reflux for 18 h. After completion of the reaction (as monitored by TLC) the reaction mixture was quenched by MeOH (15 mL) and stirred at rt for an additional 1 h. The reaction mixture was concentrated and purification by column chromatography (100-200 silica mesh, 4-6% MeOH in DCM) gave Example 2 as a pale yellow semi-solid. Yield (0.48 g, 96%); 1H NMR (400 MHz, DMSO-d6) δ 7.80 (bs, 3H), 7.24 (t, J=8.0 Hz, 1H), 6.89-6.87 (m, 2H), 6.82-6.80 (m, 1H), 5.54 (bs, 1H), 4.65 (bs, 1H), 3.87 (dd, J=11.4, 2.8 Hz, 2H), 3.81 (d, J=6.4 Hz, 2H), 3.37-3.30 (m, 2H), 2.87-2.79 (m, 2H), 2.02-1.96 (m, 1H), 1.88-1.80 (m, 2H), 1.69-1.65 (m, 2H), 1.34-1.27 (m, 2H); RP HPLC: tR=3.89 min, 95% (AUC); ESI MS m/z 266.27 [M+H]+.

Workup

  1. temperatureunder reflux for 18 h
  2. customAfter completion of the reaction (as monitored by TLC) the reaction mixture
  3. customwas quenched by MeOH (15 mL)
  4. concentrationThe reaction mixture was concentrated
  5. custompurification by column chromatography (100-200 silica mesh, 4-6% MeOH in DCM)

Sources & evidence

ORD record
ord-aef927f34a594d41b9827c031cd4e454
Source dataset
uspto-grants-2015_09
Patent number
US09133154B2

Reaction notes

Loading…