HCID 136347716, compound → HCID 136347714, compound

HRID 901339Notes

Reaction equation

HRID 901339 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[NH:14])=[CH:11][C:10]=1[CH:18]=[CH:19][C@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25](=[O:39])[C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35](=[O:38])[NH:34][CH:33]=2)=[CH:28][CH:27]=1>CO.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[OH:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([NH2:15])=[NH:14])=[CH:11][C:10]=1[CH2:18][CH2:19][C@@H:20]1[CH2:24][CH2:23][CH2:22][N:21]1[C:25](=[O:39])[C:26]1[CH:31]=[CH:30][C:29]([C:32]2[CH:37]=[CH:36][C:35](=[O:38])[NH:34][CH:33]=2)=[CH:28][CH:27]=1

Participants

4

Reactant 1

HCID 136347716HCID 136347716, compound

Product 1

HCID 136347714HCID 136347714, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

4-Hydroxy-3-(2-{1-[4-(6-oxo-1,6-dihydro-pyridin-3-yl)-benzoyl]pyrrolidin-2-(R)-yl}-vinyl)benzamidine trifluoroacetate (0.0065 g, 0.01198 mmol) in MeOH (10 mL) and 5% Pd/C (catalytic amt.) is hydrogenated using a balloon filled with H2 gas for 4 h. The reaction is filtered, evaporated and the residue is diluted with H2O (10 mL). The aqueous solution is lyopholized to give the title compound as a white solid (0.0033 g, 0.00606 mmol). 1H NMR (DMSO-d6, 300 MHz) 8.97(s, 2H), 8.60(s, 2H), 7.93-7.26(m, 8H), 6.93(d, 1H), 6.42(d, 1H), 4.15(m, 1H), 3.61-3.35(m, 1H), 2.70-2.51(m, 2H), 2.45-1.98(m, 4H), 1.93-1.55(m, 3H). MS m/z: [M+H]+=431.

Workup

  1. additionfilled with H2 gas for 4 h
  2. filtrationThe reaction is filtered
  3. customevaporated
  4. additionthe residue is diluted with H2O (10 mL)

Sources & evidence

ORD record
ord-e2dcf970988d42c58347a9fbd42b88ec
Source dataset
uspto-grants-2008_04
Patent number
US07361663B2

Reaction notes

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