HCID 117642571, compound → HCID 89625043, compound

HRID 1507761Notes

Reaction equation

HRID 1507761 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([P:22]([CH3:25])([CH3:24])=[O:23])[N:11]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)[C:10]=1[C:34]([N:36]([CH3:38])[CH3:37])=[O:35])C1C=CC=CC=1>CO.[Pd]>[CH3:24][P:22]([C:12]1[N:11]([C:26]2[CH:27]=[CH:28][C:29]([O:32][CH3:33])=[CH:30][CH:31]=2)[C:10]([C:34]([N:36]([CH3:37])[CH3:38])=[O:35])=[C:9]([OH:8])[C:13]=1[OH:14])([CH3:25])=[O:23]

Participants

4

Reactant 1

HCID 117642571HCID 117642571, compound

Product 1

HCID 89625043HCID 89625043, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3,4-bis(benzyloxy)-5-(dimethylphosphoryl)-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (66) (29 mg, 0.054 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 25° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford 5-(dimethylphosphoryl)-3,4-dihydroxy-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (UL1-125) (13 mg, 67%) as a pale yellow solid: m/z 353 (M+H)+ (ES+), 351 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.35 (s, 1H), 8.55 (s, 1H), 7.23-7.14 (m, 2H), 6.96-6.88 (m, 2H), 3.77 (s, 3H), 2.86 (br s, 6H), 1.33 (s, 3H), 1.30 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-4575243337b346d68ef8e3d7220e9f00
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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