Ammonium formate → HCID 58865616, compound

HRID 1354829Notes

Reaction equation

HRID 1354829 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@H:13]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][N:11]([C:23]2[C:28](Cl)=[C:27]([N:30]3[CH2:35][C@@H:34]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][C@@H:32]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:31]3)[N:26]=[C:25]([NH:52][C:53]3[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=3)[C:24]=2Cl)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.[Pd]>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][C@H:13]([NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12][N:11]([C:23]2[CH:28]=[C:27]([N:30]3[CH2:31][C@@H:32]([NH:44][C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:33][C@@H:34]([NH:36][C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:35]3)[N:26]=[C:25]([NH:52][C:53]3[CH:58]=[CH:57][C:56]([NH2:59])=[CH:55][CH:54]=3)[CH:24]=2)[CH2:10]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58865218HCID 58865218, compound

Product 1

HCID 58865616HCID 58865616, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4,6-Bis-((3R,5S)-3,5-bis-(tert-butoxycarbonylamino)-piperidin-1-yl)-3,5-dichloro-2-(4-aminophenyl-amino)-pyridine (167) (0.127 g, 0.144 mmol) was dissolved in MeOH (15 mL). Pd/C (0.33 g, 10%, wet) was added followed by ammonium-formate (0.66 g). The mixture was shaken in a Teflon septum capped 40 mL I-Chem vial, with occasional venting, for 16 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 on silica gel (eluting with 15–100% EtOAc in hexane for 30 minutes followed by 100% EtOAc for 10 minutes) to give the desired product (168) as an off-white powder (0.055 g, 0.0677 mmol, 47% yield). LC-MS (ESI): (exact mass: 811.5) m/e=812.6 [M+1]+.

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 on silica gel (eluting with 15–100% EtOAc in hexane for 30 minutes followed by 100% EtOAc for 10 minutes)

Sources & evidence

ORD record
ord-f4646f1fe43c4d72a1848a45178abe21
Source dataset
uspto-grants-2007_05
Patent number
US07223759B2

Reaction notes

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