5-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(cyclopent-1-en-1-yl)thiazole-4-carboxamide → 5-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-cyclopentylthiazole-4-carboxamide

HRID 522037Notes

Reaction equation

HRID 522037 reaction equation
[NH2:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH2:10][CH2:9][CH:8]=2)=[N:4][C:3]=1[C:12]([NH:14][C:15]1[CH:16]=[N:17][N:18]([CH3:29])[C:19]=1[C@@H:20]1[CH2:26][CH2:25][C@@H:24]([NH2:27])[C@@H:23]([F:28])[CH2:22][O:21]1)=[O:13]>CO.[Pd]>[NH2:1][C:2]1[S:6][C:5]([CH:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[N:4][C:3]=1[C:12]([NH:14][C:15]1[CH:16]=[N:17][N:18]([CH3:29])[C:19]=1[C@@H:20]1[CH2:26][CH2:25][C@@H:24]([NH2:27])[C@@H:23]([F:28])[CH2:22][O:21]1)=[O:13]

Participants

4

Reactant 1

HCID 867139265-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(cyclopent-1-en-1-yl)thiazole-4-carboxamide

Product 1

HCID 867139275-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-cyclopentylthiazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(cyclopent-1-en-1-yl)thiazole-4-carboxamide (Example 271) in methanol was added 10% palladium on carbon, and the mixture was stirred overnight under an atmosphere of hydrogen. The mixture was then filtered through Celite and concentrated in vacuo. HPLC purification provided 272. 1H NMR (400 MHz, DMSO-d6) δ 9.26 (s, 1H), 7.77 (s, 1H), 7.05 (s, 2H), 5.17-4.78 (m, 2H), 4.17-3.92 (m, 2H), 3.71 (s, 3H), 3.47-3.34 (m, 1H), 3.27-3.15 (m, 1H), 2.23-2.11 (m, 1H), 2.11-1.95 (m, 2H), 1.94-1.83 (m, 1H), 1.82-1.57 (m, 9H). LCMS (ES+) m/z 423 (M+1).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. concentrationconcentrated in vacuo
  3. customHPLC purification

Sources & evidence

ORD record
ord-20a01383f2a140eb8dbb9986b7d88e58
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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