HCID 117642487, compound → HCID 89625012, compound

HRID 1507745Notes

Reaction equation

HRID 1507745 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][CH3:34])=[CH:29][CH:28]=2)[C:10]=1[C:35]([O:37][CH:38]1[CH:43]([CH3:44])[CH2:42][CH2:41][CH2:40][CH:39]1[CH3:45])=[O:36])C1C=CC=CC=1>CO.[Pd]>[CH3:25][N:23]([CH3:24])[C:22]([C:12]1[N:11]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=2)[C:10]([C:35]([O:37][CH:38]2[CH:43]([CH3:44])[CH2:42][CH2:41][CH2:40][CH:39]2[CH3:45])=[O:36])=[C:9]([OH:8])[C:13]=1[OH:14])=[O:26]

Participants

4

Reactant 1

HCID 117642487HCID 117642487, compound

Product 1

HCID 89625012HCID 89625012, compoundYield 29%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2,6-dimethylcyclohexyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (45) (73 mg, 0.12 mmol) in MeOH (6 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1 mL/min at 26° C. under H2 (full H2 mode). The output was concentrated in vacuo and the crude product was purified by preparative HPLC (Waters, Acidic (0.1% formic acid), Waters X-Select Prep-C18, 5 μm, 19×50 mm column, 5-95% MeCN in Water) to afford 2,6-dimethylcyclohexyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-methoxyphenyl)-1H-pyrrole-2-carboxylate (UL1-113) (15 mg, 29%) as a yellow solid: m/z 431 (M+H)+ (ES+); 429 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.67-8.40 (m, 2H), 7.15-7.05 (m, 2H), 6.91-6.85 (m, 2H), 5.05 (br s, 1H), 3.76-3.75 (m, 3H), 2.82 (br s, 6H), 1.64-0.94 (m, 6H), 0.74-0.57 (m, 6H), 0.57-0.40 (m, 2H).

Workup

  1. customat 26° C.
  2. concentrationThe output was concentrated in vacuo
  3. customthe crude product was purified by preparative HPLC (Waters, Acidic (0.1% formic acid), Waters X-Select Prep-C18, 5 μm, 19×50 mm column, 5-95% MeCN in Water)

Sources & evidence

ORD record
ord-ad69baa5178a4f7d8f54f73c3c7d1f41
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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