HCID 117642467, compound → HCID 89614821, compound

HRID 1507731Notes

Reaction equation

HRID 1507731 reaction equation
[C:1]([C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)[C:7]([C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[C:6]([O:22]CC2C=CC=CC=2)[C:5]=1[O:30]CC1C=CC=CC=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([C:4]1[N:8]([C:9]2[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=2)[C:7]([C:17]([N:19]([CH3:21])[CH3:20])=[O:18])=[C:6]([OH:22])[C:5]=1[OH:30])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 117642467HCID 117642467, compound

Product 1

HCID 89614821HCID 89614821, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-acetyl-3,4-bis(benzyloxy)-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (34) (100 mg, 0.20 mmol) in MeOH (5 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 20° C. under H2 (full H2 mode). The output was concentrated in vacuo. The crude compound was purified by preparative HPLC (C-18 column, 21.2 mm i.d.×100 mm, 5 micron particle size, gradient 5-95% MeCN in 0.1% aq. formic acid over 16 min) to afford 5-acetyl-3,4-dihydroxy-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (UL1-091) (45 mg, 70%) as a pale yellow solid: m/z 319 (M+H)+ (ES+), 317 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.77 (s, 1H), 8.57 (s, 1H), 7.09-7.07 (m, 2H), 6.88-6.86 (m, 2H), 3.77 (s, 3H), 2.81 (br s, 6H), 2.05 (s, 3H).

Workup

  1. customat 20° C.
  2. concentrationThe output was concentrated in vacuo
  3. customThe crude compound was purified by preparative HPLC (C-18 column, 21.2 mm i.d.×100 mm, 5 micron particle size, gradient 5-95% MeCN in 0.1% aq. formic acid over 16 min)

Sources & evidence

ORD record
ord-04b393a0a52f4aaeb18eb1547d3b6277
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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