2-(3-Oxobutyl)isoindoline-1,3-dione → HCID 68972829, compound

HRID 1726134Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:24]2[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=2)[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]#[N:23])[N:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O=[C:33]([CH3:47])[CH2:34][CH2:35][N:36]1C(=O)C2C(=CC=CC=2)C1=O>>[NH2:36][CH2:35][CH2:34][CH:33]([N:8]1[CH2:9][CH2:10][CH:11]([CH:14]([C:24]2[CH:25]=[CH:26][C:27]([C:30]#[N:31])=[CH:28][CH:29]=2)[O:15][C:16]2[N:17]=[C:18]([C:22]#[N:23])[CH:19]=[CH:20][CH:21]=2)[CH2:12][CH2:13]1)[CH3:47]

Participants

Reactant 2

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dione

HCID 68971431HCID 68971431, compound

Product 1

HCID 68972829HCID 68972829, compound

Procedure

Using general procedure C with 4-[(4-cyano-phenyl)-(6-cyano-pyridin-2-yloxy)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 43) (200 mg, 0.48 mmol), then general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (168 mg, 0.77 mmol) and then using general procedure D afforded 6-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-cyano-phenyl)-methoxy]-pyridine-2-carbonitrile as a colourless syrup (40 mg, 22% over 3 steps).

Sources & evidence

ORD record: ord-5a88d0ea9527422091fb5e55f99e9c88
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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