HCID 71599636, compound → HCID 71599112, compound

HRID 1507686Notes

Reaction equation

HRID 1507686 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[O:23])[N:11]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:10]=1[C:37]([N:39]([CH2:42][CH3:43])[CH2:40][CH3:41])=[O:38])C1C=CC=CC=1>CO.C(Cl)Cl.[Pd]>[CH2:42]([N:39]([CH2:40][CH3:41])[C:37]([C:10]1[N:11]([C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)[C:12]([C:22]([N:24]([CH2:25][CH3:26])[CH2:27][CH3:28])=[O:23])=[C:13]([OH:14])[C:9]=1[OH:8])=[O:38])[CH3:43]

Participants

4

Reactant 1

HCID 71599636HCID 71599636, compound

Product 1

HCID 71599112HCID 71599112, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of 3,4-bis(benzyloxy)-N2,N2,N5,N5-tetraethyl-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxamide UL1-046 (50 mg, 0.086 mmol) in methanol/DCM (4 mL/4 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 25° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford N2,N2,N5,N5-tetraethyl-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2,5-dicarboxamide (UL1-003) (32 mg, 93%) as a light yellow solid: m/z 404 (M+H)+ (ES+); 402 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ 8.26 (s, 2H), 6.96-6.88 (m, 2H), 6.87-6.81 (m, 2H), 3.72 (s, 3H), 3.27 (q, J=7.1 Hz, 8H), 0.96 (t, J=7.0 Hz, 12H).

Workup

  1. customat 25° C.
  2. concentrationThe output was concentrated in vacuo

Sources & evidence

ORD record
ord-f24349ee15674bb1a34a8f0ac6e2840a
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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