HCID 71599802, compound → HCID 71599368, compound

HRID 1507693Notes

Reaction equation

HRID 1507693 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([NH:37][CH2:38][CH3:39])=[O:36])C1C=CC=CC=1>CO.[Pd]>[CH2:38]([NH:37][C:35]([C:10]1[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:12]([C:22]([N:24]([CH3:26])[CH3:25])=[O:23])=[C:13]([OH:14])[C:9]=1[OH:8])=[O:36])[CH3:39]

Participants

4

Reactant 1

HCID 71599802HCID 71599802, compound

Product 1

HCID 71599368HCID 71599368, compoundYield 86.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3,4-bis(benzyloxy)-N2-ethyl-1-(4-methoxyphenyl)-N5,N5-dimethyl-1H-pyrrole-2,5-dicarboxamide (UL1-055) (118 mg, 0.22 mmol) in methanol (4.5 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 30° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford N2-ethyl-3,4-dihydroxy-1-(4-methoxyphenyl)-N5,N5-dimethyl-1H-pyrrole-2,5-dicarboxamide (UL1-024) (66 mg, 82%) as a brown solid: m/z 348 (M+H)+ (ES+); 346 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.44 (s, 1H), 8.42 (s, 1H), 7.10-7.03 (m, 1H), 7.02-6.97 (m, 2H), 6.86-6.77 (m, 2H), 3.75 (s, 3H), 3.14-3.06 (m, 2H), 2.81 (br s, 6H), 0.97 (t, J=7.2 Hz, 3H).

Workup

  1. customat 30° C.
  2. concentrationThe output was concentrated in vacuo

Sources & evidence

ORD record
ord-7f3f791192004e82b925445849a8c0c1
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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