HCID 131724830, compound → HCID 87582205, compound

HRID 1815056Notes

Reaction equation

HRID 1815056 reaction equation
[I-].[Cl:2][C:3]1[CH:42]=[N:41][CH:40]=[C:39]([Cl:43])[C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:21][C:22]2[C:25]3([CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)[C:24](=[O:31])[C:23]=2[C:32]2[CH2:33][N:34]([CH3:38])[CH:35]=[CH:36][CH:37]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1)=[O:6].[H][H]>CCO.[Pt](=O)=O>[Cl:43][C:39]1[CH:40]=[N:41][CH:42]=[C:3]([Cl:2])[C:4]=1[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C@H:15]([NH:21][C:22]2[C:25]3([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30]3)[C:24](=[O:31])[C:23]=2[CH:32]2[CH2:37][CH2:36][CH2:35][N:34]([CH3:38])[CH2:33]2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:10][CH:9]=1)=[O:6]

Participants

5

Reactant 2

HCID 131724830HCID 131724830, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 87582205HCID 87582205, compoundYield 100.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

The compound of Example 86 (127 mg, 0.21 mmol) was dissolved in EtOH (10 ml) and hydrogenated over platinum dioxide (50 mg) at room temperature and 1 atmosphere hydrogen for 5 days. The catalyst was removed by evaporation in vacuo to afford the title compound as a yellow oil (129 mg, 100%). δH (DMSO d6) 10.48 (1H, brs), 8.70 (2H, s), 7.59 (2H, d, J 8.1 Hz), 7.30 (2H, d, J 8.1 Hz), 4.25 (1H, m), 4.22 (2H, q, J 4.0 Hz), 3.23 (1H, m), 3.08 (1H, m), 1.70-1.50 (22H, m), 1.26 (3H, m); m/z (ES+, 70V) 613.2 (MH+).

Workup

  1. customThe catalyst was removed by evaporation in vacuo

Sources & evidence

ORD record
ord-4e7036c8952b4113966e47181e53ddad
Source dataset
uspto-grants-2005_04
Patent number
US06878718B2

Reaction notes

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