HCID 67386829, compound → HCID 53390115, compound

HRID 2408847Notes

Reaction equation

HRID 2408847 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15]([N:17]3[CH2:22][CH2:21][N:20](C(OCC4C=CC=CC=4)=O)[CH2:19][CH2:18]3)=[O:16])[C:9]2=[O:33])=[CH:4][CH:3]=1>O1CCCC1>[F:40][C:37]1[CH:38]=[CH:39][C:34]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:13][CH2:12][CH2:11][N:10]([CH2:14][C:15](=[O:16])[N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)[C:9]2=[O:33])=[CH:35][CH:36]=1

Participants

3

Reactant 1

HCID 67386829HCID 67386829, compound

Product 1

HCID 53390115HCID 53390115, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A 50 mL pressure bottle was charged with tetrahydrofuran (10 mL), the product of Example 23E (0.500 g, 0.913 mmol) and 20% Pd(OH)2—C, wet (0.100 g, 0.712 mmol). The reaction mixture was stirred at 50° C. under an atmosphere of 30 psi H2 for 15 minutes. The mixture was filtered through a nylon membrane and concentrated in vacuo. The crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; 2N NH4OH in CH3OH/CH2Cl2, 2:98, eluant) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.30-7.21 (m, 4H), 7.15-7.05 (m, 4H), 4.17 (s, 2H), 3.45-3.24 (m, 7H), 2.66 (d, J=3.6, 4H), 2.55-2.46 (m, 2H), 1.74-1.60 (m, 2H); MS (DCI+) m/z 414 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane
  2. concentrationconcentrated in vacuo
  3. customThe crude product was purified by chromatography on silica gel (Analogix Intelliflash 280; 2N NH4OH in CH3OH/CH2Cl2, 2:98, eluant)

Sources & evidence

ORD record
ord-3e72f055ec674935b1fa1e86ab5e7a84
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

Loading…