HCID 57814068, compound → HCID 57813947, compound

HRID 564403Notes

Reaction equation

HRID 564403 reaction equation
[CH3:1][C:2](=[CH2:33])[CH2:3][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][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=1>CO>[CH2:3]([O:4][C@@H:5]1[CH2:9][N:8]([CH:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)[CH2:7][C@H:6]1[NH:16][C:17](=[O:32])[CH2:18][NH:19][C:20](=[O:31])[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=1)[CH:2]([CH3:33])[CH3:1]

Participants

3

Reactant 1

HCID 57814068HCID 57814068, compound

Product 1

HCID 57813947HCID 57813947, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of rel-N-(2-{[(3R,4R)-4-[(2-methylprop-2-en-1-yl)oxy]-1-(tetrahydro-2H-pyran-4-yl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide in methanol (400 μL) was added and Palladium (10%) on Carbon (50 mg) the was purged with hydrogen gas for two minutes; the reaction was then subjected to 1 atmosphere of hydrogen gas overnight. The flask was purged with Argon; the mixture was filtered, then purified by preparative HPLC to afford the title compound as a white solid. 1H-NMR (MeOD) δ: 0.893 (d, J=1.63 Hz, 3H), 0.915 (d, J=1.63 Hz, 3H), 1.51 (m, 2H), 1.77-1.87 (m, 3H), 2.44 (m, 1H), 2.64 (m, 1H), 2.71 (m, 1H), 3.10 (m, 2H), 3.21 (m, 1H), 3.38 (m, 2H), 3.87 (m, 1H), 3.95 (m, 3H), 4.04 (s, 2H), 4.29 (m, 1H), 7.70 (t, J=7.7 Hz, 1H), 7.87 (d, J=7.7 Hz, 1H), 8.15 (d, J=7.7 Hz, 1H), 8.22 (s, 1H) MS m/z: 472 (M+1).

Workup

  1. customPalladium (10%) on Carbon (50 mg) the was purged with hydrogen gas for two minutes
  2. customwas then subjected to 1 atmosphere of hydrogen gas overnight
  3. customThe flask was purged with Argon
  4. filtrationthe mixture was filtered
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7733b828b32c4338a6d8a39591115d38
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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