HCID 89610494, compound → HCID 71599455, compound

HRID 1507700Notes

Reaction equation

HRID 1507700 reaction equation
C([O:8][C:9]1[C:13]([O:14]CC2C=CC=CC=2)=[C:12]([C:22]#[N:23])[N:11]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:10]=1[C:32]([N:34]([CH3:36])[CH3:35])=[O:33])C1C=CC=CC=1>CO.[Pd]>[C:22]([C:12]1[N:11]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C:10]([C:32]([N:34]([CH3:35])[CH3:36])=[O:33])=[C:9]([OH:8])[C:13]=1[OH:14])#[N:23]

Participants

4

Reactant 1

HCID 89610494HCID 89610494, compound

Product 1

HCID 71599455HCID 71599455, compoundYield 21.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-Bis(benzyloxy)-5-cyano-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (12) (85 mg, 0.17 mmol) in methanol (2 mL) was passed through a Thales ‘H-cube’ cartridge (10% Pd/C) at a flow rate of 1.5 mL/min at 25° C. under H2 (full H2 mode). The output was concentrated in vacuo to afford 5-cyano-3,4-dihydroxy-1-(4-methoxyphenyl)-N,N-dimethyl-1H-pyrrole-2-carboxamide (UL1-031) (11 mg, 21%) as a yellow solid: m/z 302 (M+H)+ (ES+); 300 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 9.80 (s, 1H), 8.80 (s, 1H), 7.21-7.11 (m, 2H), 7.03-6.93 (m, 2H), 3.79 (s, 3H), 2.88 (br s, 6H).

Workup

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

Sources & evidence

ORD record
ord-2833eeac6e464512b036077f7bed6b5c
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

Loading…