Ammonium formate → HCID 58865722, compound

HRID 1354826Notes

Reaction equation

HRID 1354826 reaction equation
Cl[C:2]1[C:3]([N:39]2[CH2:44][C@@H:43]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:42][C@@H:41]([NH:53][C:54]([O:56][C:57]([CH3:60])([CH3:59])[CH3:58])=[O:55])[CH2:40]2)=[N:4][C:5]([N:17]2[CH2:22][C@@H:21]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C@@H:19]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:18]2)=[C:6](Cl)[C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=1.C([O-])=O.[NH4+]>CO.[Pd]>[C:57]([O:56][C:54]([NH:53][C@@H:41]1[CH2:42][C@H:43]([NH:45][C:46]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])=[O:47])[CH2:44][N:39]([C:3]2[CH:2]=[C:7]([NH:8][C:9]3[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=3)[CH:6]=[C:5]([N:17]3[CH2:22][C@@H:21]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][C@@H:19]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:18]3)[N:4]=2)[CH2:40]1)=[O:55])([CH3:58])([CH3:59])[CH3:60]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58865789HCID 58865789, compound

Product 1

HCID 58865722HCID 58865722, compoundYield 42.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-(3,5-dichloro-2,6-bis-((3R,5S)-3,5-bis-(tert-butoxycarbonylamino)-piperidin-1-yl)-pyridin-4-yl)-benzene-1,4-diamine (140) (0.205 g, 0.233 mmol) was dissolved in MeOH (15 mL). Pd/C (1 g, 10%, wet) was added followed by ammonium-formate (2 g). The mixture was shaken in a Teflon septum capped 40 mL I-Chem vial, with occasional venting, for 3 hours. LC-MS indicated complete de-chlorination at this point. The mixture was filtered through a plug of Celite and the filtrate was concentrated and purified by flash chromatography using a gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane in 30 minutes followed by 100% EtOAc in 10 minutes) to give the desired product (141) as a yellow/green oil (0.08 g, 0.098 mmol, 42.3% yield). LC-MS (ESI): (exact mass: 811.50) m/e=812.7 [M+1]+ (100%).

Workup

  1. customcapped 40 mL I-Chem vial
  2. filtrationThe mixture was filtered through a plug of Celite
  3. concentrationthe filtrate was concentrated
  4. custompurified by flash chromatography
  5. customa gradient of hexane and EtOAc (eluding with 15–100% EtOAc in hexane in 30 minutes followed by 100% EtOAc in 10 minutes)

Sources & evidence

ORD record
ord-b914c9a4f4fe48639b15e025101c24e7
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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