Pyridine → (S)-Methyl 2-(6-(5-(4-tert-butylbenzamido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

HRID 403995Notes

Reaction equation

HRID 403995 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][N:13]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[C:14]3=[O:17])=[CH:10][CH:9]=2)=[N:6][CH:7]=1.N1C=CC=CC=1.[C:32]([C:36]1[CH:44]=[CH:43][C:39]([C:40](Cl)=[O:41])=[CH:38][CH:37]=1)([CH3:35])([CH3:34])[CH3:33]>ClCCl>[C:32]([C:36]1[CH:37]=[CH:38][C:39]([C:40]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:16]=[C:15]4[C:11]([CH2:12][N:13]([C@@H:18]([CH:23]([CH3:25])[CH3:24])[C:19]([O:21][CH3:22])=[O:20])[C:14]4=[O:17])=[CH:10][CH:9]=3)=[N:6][CH:7]=2)=[O:41])=[CH:43][CH:44]=1)([CH3:35])([CH3:33])[CH3:34]

Participants

5

Reactant 3

HCID 1049PyridineHCID 743724-tert-Butylbenzoyl chlorideHCID 131731548(S)-Methyl 2-(6-(5-aminopyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Product 1

HCID 131731552(S)-Methyl 2-(6-(5-(4-tert-butylbenzamido)pyridin-2-yl)-1-oxoisoindolin-2-yl)-3-methylbutanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of compound of example 392 (100 mg, 0.295 mmol) in dichloromethane (3 mL), pyridine (70.53 mg, 0.885 mmol) was added and stirred for 5 min. To the reaction mixture, 4-tert-butylbenzoyl chloride (87.27 mg, 0.443 mmol) was added and stirred for about 16 h. After completion of the reaction, the solvent was evaporated and the crude material obtained was triturated with diethyl ether to obtain the title compound, which was filtered and dried.

Workup

  1. stirringstirred for about 16 h
  2. customAfter completion of the reaction
  3. customthe solvent was evaporated
  4. customthe crude material obtained
  5. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-ac90ce3a00e446b29e800d1a9160679e
Source dataset
uspto-grants-2014_06
Patent number
US08748426B2

Reaction notes

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