HCID 57803292, compound → HCID 57803416, compound

HRID 2103381Notes

Reaction equation

HRID 2103381 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([C:9](=[O:24])[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[C@H:6]([CH3:25])[CH2:5]1)=[N+]=[N-]>C(O)C.[Pd]>[NH2:1][C@@H:4]1[CH2:8][N:7]([C:9](=[O:24])[CH2:10][NH:11][C:12](=[O:23])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[CH:14]=2)[C@H:6]([CH3:25])[CH2:5]1

Participants

4

Reactant 1

HCID 57803292HCID 57803292, compound

Product 1

HCID 57803416HCID 57803416, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

N-{2-[(2R,4S)-4-Azido-2-methylpyrrolidin-1-yl]-2-oxoethyl}-3-(trifluoromethyl)benzamide (1.33 g, 3.74 mmol) was dissolved in ethanol (50 mL) and then 10% Pd—C (130 mg) was added to the solution. The flask was purged with hydrogen and then stirred under an atmosphere of hydrogen using a balloon for four hours at which point, TLC indicated complete consumption of starting material. The reaction was then flushed with nitrogen and filtered through Celite on a glass frit and washed with methanol. The filtrate was concentrated to give the desired amine as a dark brown oil, 1.21 g (98%). LC/MS (M+H)+ m/z=330.1. 1H NMR (CDCl3) δ 8.12 (s, 1H), 8.02 (d, 1H), 7.77 (d, 1H), 7.58 (t, 1H), 7.37 (bs, 1H), 4.16 (m, 3H), 3.72 (m, 1H), 3.61 (m, 1H), 3.15 (m, 1H), 2.44 (m, 1H), 1.70-1.20 (m, 3H), 1.43 (d, 3H); 19F NMR (CDCl3) δ −63.12 (s).

Workup

  1. customThe flask was purged with hydrogen
  2. customconsumption of starting material
  3. customThe reaction was then flushed with nitrogen
  4. filtrationfiltered through Celite on a glass frit
  5. washwashed with methanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-510d23ed9d42428b852bef33d08c6bc4
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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