HCID 57949399, compound → HCID 57949598, compound

HRID 2427771Notes

Reaction equation

HRID 2427771 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16]2[CH:17]=[C:18]3[C:22](=[C:23]([Cl:25])[CH:24]=2)[C:21](=[O:26])[N:20]([CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][CH:29]=2)[CH2:19]3)[CH2:10][CH2:9]1)=O)(C)(C)C>C(O)=O>[Cl:25][C:23]1[CH:24]=[C:16]([NH:15][CH2:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:17]=[C:18]2[C:22]=1[C:21](=[O:26])[N:20]([CH2:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:37])([F:36])[F:38])=[CH:30][CH:29]=1)[CH2:19]2

Participants

3

Reactant 1

HCID 57949399HCID 57949399, compound

Product 1

HCID 57949598HCID 57949598, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

4- {[7-Chloro-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindol-5-ylamino]-methyl}-piperidine-1-carboxylic acid tert-butyl ester (47 mg, 0.0848 mmol) was stirred in formic acid (4 mL) overnight at room temperature and the solvent was removed under vacuum. The resulting residue was triturated with ether to provide the title compound (29 mg, 74%) as a colorless solid. 1H NMR (300 MHz, CDCl3): δ 8.44 (s, 2H), 7.59 (s, 1H), 7.53 (s, 1H), 7.46 (d, 2H), 7.29 (d, 2H), 4.84 (s, 2H), 4.41 (s, 2H), 4.08 (s, 2H), 3.43-3.39 (m, 2H), 3.03-2.94 (m, 2H), 2.77 (d, 2H), 2.05-2.00 (m, 2H), 1.46-1.42 (m, 2H).

Workup

  1. customthe solvent was removed under vacuum
  2. customThe resulting residue was triturated with ether

Sources & evidence

ORD record
ord-b29109c5927b4cb48eec7c69f7104848
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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