HCID 86713960, compound → HCID 86713961, compound

HRID 522069Notes

Reaction equation

HRID 522069 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 86713960HCID 86713960, compound

Product 1

HCID 86713961HCID 86713961, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-amino-N-(5-((2S,5R,6S)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(cyclopent-1-en-1-yl)thiazole-4-carboxamide (Example 333) in methanol was added 10% palladium on carbon, and the mixture was stirred under an atmosphere of hydrogen overnight. After filtration and in vacuo concentration, purification by HPLC provided the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.13 (s, 1H), 7.79 (s, 1H), 7.05 (s, 2H), 4.83-4.74 (m, 1H), 4.48-4.30 (m, 1H), 4.26-4.12 (m, 1H), 4.11-3.91 (m, 1H), 3.74 (s, 3H), 2.07-1.97 (m, 3H), 1.88-1.52 (m, 11H). LCMS (ES+) m/z 423 (M+1).

Workup

  1. filtrationAfter filtration
  2. concentrationin vacuo concentration, purification by HPLC

Sources & evidence

ORD record
ord-eb812cd615e34f16836d6b09c6a7b353
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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