(S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate → (S)-7-amino-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-N-methylheptanamide

HRID 2202562Notes

Reaction equation

HRID 2202562 reaction equation
[CH3:1][O:2][C:3]1[C:12]([C:13]2[O:17][C:16]([C@@H:18]([NH:28]C(=O)OCC3C=CC=CC=3)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:26][CH3:27])=[O:25])=[N:15][CH:14]=2)=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=1>CCOC(C)=O.CO.[Pd]>[NH2:28][C@H:18]([C:16]1[O:17][C:13]([C:12]2[C:3]([O:2][CH3:1])=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][CH:8]=[CH:7][CH:6]=3)=[CH:14][N:15]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([NH:26][CH3:27])=[O:25]

Participants

4

Reactant 1

HCID 90149176(S)-benzyl (1-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-7-(methylamino)-7-oxoheptyl)carbamate

Product 1

HCID 90120016(S)-7-amino-7-(5-(2-methoxyquinolin-3-yl)oxazol-2-yl)-N-methylheptanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584119Ethylacetate methanolSolvent

Procedure

F6 was dissolved in EtOAc/MeOH (1:1, 0.025 M) and treated with Pd/C (10% w/w). Mixture was purged with N2 and stirred under H2 atmosphere at room temperature for 48 h. Then, reaction mixture was filtered through a pad of Solka-Floc® and filtrate was concentrated under vacuum to give the title compound as pale yellow solid which was used as such in the next step. MS (ES+) C21H26N4O3: 383 (M+H)+.

Workup

  1. customMixture was purged with N2
  2. customThen, reaction mixture
  3. filtrationwas filtered through a pad of Solka-Floc® and filtrate
  4. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-a718fe4584d842f48ac6c1e0cee04df3
Source dataset
uspto-grants-2016_06
Patent number
US09365541B2

Reaction notes

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