HCID 67004980, compound → HCID 67005303, compound

HRID 564410Notes

Reaction equation

HRID 564410 reaction equation
[CH2:1]([O:4][C@@H:5]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:7][C@H:6]1[NH:16][C:17](=[O:32])[CH2:18][C:19]1[NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:31])([F:30])[F:29])[C:21]=2[N:20]=1)[CH:2]=[CH2:3]>CO.[Pd]>[CH2:1]([O:4][C@@H:5]1[CH2:9][N:8]([CH:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH2:7][C@H:6]1[NH:16][C:17](=[O:32])[CH2:18][C:19]1[NH:23][C:22]2[CH:24]=[CH:25][CH:26]=[C:27]([C:28]([F:29])([F:31])[F:30])[C:21]=2[N:20]=1)[CH2:2][CH3:3]

Participants

4

Reactant 1

HCID 67004980HCID 67004980, compound

Product 1

HCID 67005303HCID 67005303, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of rel-N-[(3R,4R)-4-(allyloxy)-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]-2-[4-(trifluoromethyl)-1H-benzimidazol-2-yl]acetamide in methanol was added Pd/C and the reaction was exposed to 1 atm H2 overnight. The reaction mixture was filtered and concentrated to afford rel-N-[(3R,4R)-4-propoxy-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]-2-[4-(trifluoromethyl)-1H-benzimidazol-2-yl]acetamide as a white solid. 1H-NMR (CDCl3) δ: 0.87 (t, 3H), 1.48-1.58 (m, 4H), 1.74 (m, 2H), 1.89 (m, 2H), 2.24-2.35 (m, 2H), 2.73 (m, 2H), 3.31-3.40 (m, 4H), 3.56 (m, 1H), 3.73 (m, 1H), 3.92-3.98 (m, 2H), 3.92 (s, 2H), 4.28 (m, 1H), 7.14 (b, 1H), 7.30 (t, J=7.9 Hz, 1H), 7.49 (d, J=7.3 Hz, 1H). MS m/z: 455 (M+1).

Workup

  1. customwas exposed to 1 atm H2 overnight
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3feee6006f6a4063a61ed96c1ac27abc
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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