2-(3-Oxobutyl)isoindoline-1,3-dione → HCID 86602128, compound

HRID 1726133Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[N:25]=2)[C:15]2[CH:20]=[CH:19][C:18]([C:21]#[N:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O=[C:32]([CH3:46])[CH2:33][CH2:34][N:35]1C(=O)C2C(=CC=CC=2)C1=O>>[NH2:35][CH2:34][CH2:33][CH:32]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([O:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[N:25]=2)[C:15]2[CH:16]=[CH:17][C:18]([C:21]#[N:22])=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)[CH3:46]

Participants

Reactant 2

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

HCID 86602129HCID 86602129, compound

Product 1

HCID 86602128HCID 86602128, compound

Procedure

Using general procedure C with 4-[(6-chloro-pyridin-2-yloxy)-(4-cyano-phenyl)-methyl]-piperidine-1-carboxylic acid tert-butyl ester (236 mg, 0.55 mmol), then general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (203 mg, 0.93 mmol) and then using general procedure D afforded 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(6-chloro-pyridin-2-yloxy)-methyl]-benzonitrile as a colourless syrup (65 mg, 37% over 3 steps).

Sources & evidence

ORD record: ord-653c585b255647d3844e4e0ba6003804
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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