HCID 57814021, compound → HCID 67004446, compound

HRID 564362Notes

Reaction equation

HRID 564362 reaction equation
[F:1][C:2]([F:44])([F:43])[C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][CH:42]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:39]=[CH:38][C:27]([C:28]([O:30]CC4C=CC=CC=4)=[O:29])=[CH:26][CH:25]=3)[CH2:20][CH2:19]2)[CH2:14]1)=[O:11])=[O:7].[H][H]>CO.[Pd]>[F:44][C:2]([F:1])([F:43])[C:3]1[CH:4]=[C:5]([CH:40]=[CH:41][CH:42]=1)[C:6]([NH:8][CH2:9][C:10]([NH:12][C@@H:13]1[CH2:17][CH2:16][N:15]([CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:25]=[CH:26][C:27]([C:28]([OH:30])=[O:29])=[CH:38][CH:39]=3)[CH2:20][CH2:19]2)[CH2:14]1)=[O:11])=[O:7]

Participants

5

Reactant 2

HCID 57814021HCID 57814021, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 67004446HCID 67004446, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

In a round-bottom flask, a solution of benzyl 4-(4-{(3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-1-yl}piperidin-1-yl)benzoate (120 mg, 0.20 mmol) in methanol (400 μL) and Palladium (10%) on Carbon (50 mg) was purged with hydrogen gas for two minutes; the reaction was then subjected to 1 atmosphere of hydrogen gas for two hours. The flask was purged with argon, then the mixture was filtered and concentrated to afford 4-(4-{(3R)-3-[({[3-(trifluoromethyl)benzoyl]amino}acetyl)amino]pyrrolidin-1-yl}piperidin-1-yl)benzoic acid (101 mg, 96%) as an off-white solid. 1H-NMR (CD3OD) δ: 1.60-1.98 (m, 4H), 1.90-2.40 (m, 4H), 2.85-3.05 (m, 3H), 3.38-4.10 (m, 8H), 4.40-5.58 (m, 1H), 7.01 (d, J=9.0 Hz, 2H), 7.70 (t, J=8.1 Hz, 2H), 7.84-7.90 (m, 1H), 7.89 (d, J=8.7 Hz, 2H), 8.15 (d, J=7.8 Hz, 1H), 8.22 (s, 1H). MS m/z: 519 (M+1).

Workup

  1. customThe flask was purged with argon
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1eb49d5441264ff5913339e00066f869
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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