Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate → ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate

HRID 1507736Notes

Reaction equation

HRID 1507736 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][CH2:34][CH2:35][CH2:36][N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[CH:29][CH:28]=2)[C:10]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44])C1C=CC=CC=1>CO.[Pd]>[CH3:25][N:23]([CH3:24])[C:22]([C:12]1[N:11]([C:27]2[CH:28]=[CH:29][C:30]([O:33][CH2:34][CH2:35][CH2:36][N:37]3[CH2:38][CH2:39][O:40][CH2:41][CH2:42]3)=[CH:31][CH:32]=2)[C:10]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:9]([OH:8])[C:13]=1[OH:14])=[O:26]

Participants

4

Reactant 1

HCID 117642460Ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate

Product 1

HCID 89625022ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylateYield 27.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of ethyl 3,4-bis(benzyloxy)-5-(dimethylcarbamoyl)-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate (37) (105 mg, 0.16 mmol) in MeOH (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, and a solid was collected by filtration after trituration with isohexane to afford ethyl 5-(dimethylcarbamoyl)-3,4-dihydroxy-1-(4-(3-morpholinopropoxy)phenyl)-1H-pyrrole-2-carboxylate (UL1-102) (20 mg, 25%) as a yellow solid: m/z 462 (M+H)+ (ES+), 460 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 8.58 (s, 1H), 8.44 (s, 1H), 7.05-6.99 (m, 2H), 6.86-6.82 (m, 2H), 4.03-3.95 (m, 4H), 3.61-3.53 (m, 4H), 2.82 (br s, 6H), 2.45-2.34 (m, 6H), 1.93-1.81 (m, 2H), 0.98 (t, J=7.0 Hz, 3H).

Workup

  1. customat 25° C.
  2. concentrationThe output was concentrated in vacuo
  3. filtrationa solid was collected by filtration after trituration with isohexane

Sources & evidence

ORD record
ord-272ac08336684b37863834261b3416ce
Source dataset
uspto-grants-2015_12
Patent number
US09221756B2

Reaction notes

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