HCID 117642415, compound → HCID 89625023, compound

HRID 1507743Notes

Reaction equation

HRID 1507743 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22](=[O:26])[N:23]([CH3:25])[CH3:24])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:29][CH:28]=2)[C:10]=1[C:41]([O:43][CH2:44][CH3:45])=[O:42])C1C=CC=CC=1>CO.[Pd]>[CH3:25][N:23]([CH3:24])[C:22]([C:12]1[N:11]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][CH2:36][S:37]([CH3:40])(=[O:39])=[O:38])=[CH:31][CH:32]=2)[C:10]([C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:9]([OH:8])[C:13]=1[OH:14])=[O:26]

Participants

4

Reactant 1

HCID 117642415HCID 117642415, compound

Product 1

HCID 89625023HCID 89625023, compoundYield 58.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-(methylsulfonyl)propoxy)phenyl)-1H-pyrrole-2-carboxylate (44) (95 mg, 0.15 mmol) in MeOH (4 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 40° C. under H2 (full H2 mode). The output was concentrated in vacuo, and the compound was purified by preparative HPLC (C-18 column, 21.2 mm i.d.×100 mm, 5 micron particle size, gradient 15-40% MeCN in 0.1% aq. formic acid over 16 min) to afford ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-(3-(methylsulfonyl)propoxy)phenyl)-1H-pyrrole-2-carboxylate (UL1-110) (40 mg, 58%) as a yellow solid: m/z 455 (M+H)+ (ES+); 453 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.58 (s, 1H), 8.45 (s, 1H), 7.07-7.02 (m, 2H), 6.89-6.84 (m, 2H), 4.08 (t, J=7.2 Hz, 2H), 3.99 (q, J=7.1 Hz, 2H), 3.29-3.25 (m, 2H), 3.02 (s, 3H), 2.92-2.71 (br s, 6H), 2.21-2.07 (m, 2H), 0.99 (t, J=7.1 Hz, 3H).

Workup

  1. customat 40° C.
  2. concentrationThe output was concentrated in vacuo
  3. customthe compound was purified by preparative HPLC (C-18 column, 21.2 mm i.d.×100 mm, 5 micron particle size, gradient 15-40% MeCN in 0.1% aq. formic acid over 16 min)

Sources & evidence

ORD record
ord-ab1a9a1ff10649acbd0cd25d41122cbf
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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