HCID 10188251, compound → HCID 21961485, compound

HRID 2211672Notes

Reaction equation

HRID 2211672 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([NH:23][C:24](=[O:40])[C:25]4[CH:30]=[CH:29][CH:28]=[N:27][C:26]=4[NH:31][CH2:32][C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=4)[CH:21]=3)[C:16]([CH3:42])([CH3:41])[CH2:15]2)[CH2:10][CH2:9]1)(OC(C)(C)C)=O>Cl.CCOC(C)=O>[CH3:41][C:16]1([CH3:42])[C:17]2[C:22](=[CH:21][C:20]([NH:23][C:24](=[O:40])[C:25]3[CH:30]=[CH:29][CH:28]=[N:27][C:26]=3[NH:31][CH2:32][C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)=[CH:19][CH:18]=2)[N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:15]1

Participants

4

Reactant 1

HCID 10188251HCID 10188251, compound

Product 1

HCID 21961485HCID 21961485, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[1-(1-Boc-piperidin-4-yl)-3,3-dimethyl-2,3-dihydro-1H-indol-6-yl]-2-(4-fluoro-benzylamino)-nicotinamide (Example 47) was dissolved in a mixture of conc. HCl and EtOAc and stirred at RT for 1.5 h. The mixture was concentrated in vacuo and the residue was partitioned between EtOAc and 1 N NaOH. The organic layer was removed, washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to provide a yellow solid. M+H 474.3. Calc'd for C28H32FN5O: 473.3.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between EtOAc and 1 N NaOH
  3. customThe organic layer was removed
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide a yellow solid

Sources & evidence

ORD record
ord-c09a4ce20fa14aaaafb6cc6e52f9553e
Source dataset
uspto-grants-2006_09
Patent number
US07101868B2

Reaction notes

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