Pyridine → HCID 178430146, compound

HRID 1864713Notes

Reaction equation

HRID 1864713 reaction equation
[Cl:1][C:2]1[C:3]([CH3:29])=[C:4](/[N:10]=[C:11]2\[N:12]([C:27]#[N:28])[CH2:13][C@@H:14]3[C@H:18]([O:19][Si](C(C)(C)C)(C)C)[CH2:17][CH2:16][N:15]\23)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].N1C=CC=CC=1.C1C[O:39]CC1>>[Cl:1][C:2]1[C:3]([CH3:29])=[C:4](/[N:10]=[C:11]2\[N:12]([C:27]([NH2:28])=[O:39])[CH2:13][C@@H:14]3[C@H:18]([OH:19])[CH2:17][CH2:16][N:15]\23)[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

Participants

4

Reactant 3

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 178430144HCID 178430144, compound

Product 1

HCID 178430146HCID 178430146, compound

Procedure

Compound 12A (30.0 mg, 0.0699 mmol) was dissolved in THF (1 mL) and HF/pyridine (˜2.3:1, 0.075 mL) was added. After stirring at rt overnight, the reaction was concentrated and purified via preparative HPLC (YMC ODS C-18, 21.2×100 mm, eluting with 50-100% solvent B (A=90% H2O-10% MeOH-0.1% TFA and B=10% H2O-90% MeOH-0.1% TFA) over 10 min; Flow rate at 20 mL/min; UV detection at 220 nm. The peaks were collected, combined and repurified via preparative HPLC (YMC ODS C-18, 21.2×100 mm, eluting with 30-100% solvent B (A=90% H2O-10% MeOH-0.1% TFA and B=10% H2O-90% MeOH-0.1% TFA) over 10 min; Flow rate at 20 mL/min; UV detection at 220 nm to provide compound 12B (8.0 mg) as a clear film. MS: m/z 334 [M+H]+.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified via preparative HPLC (YMC ODS C-18, 21.2×100 mm
  3. washeluting with 50-100% solvent B (A=90% H2O-10% MeOH-0.1% TFA and B=10% H2O-90% MeOH-0.1% TFA) over 10 min
  4. customThe peaks were collected
  5. customrepurified via preparative HPLC (YMC ODS C-18, 21.2×100 mm
  6. washeluting with 30-100% solvent B (A=90% H2O-10% MeOH-0.1% TFA and B=10% H2O-90% MeOH-0.1% TFA) over 10 min

Sources & evidence

ORD record
ord-698474b7a769471baae4d50ccd0ffae5
Source dataset
uspto-grants-2009_12
Patent number
US07625923B2

Reaction notes

Loading…