2-(3-Oxobutyl)isoindoline-1,3-dione → HCID 68970630, compound

HRID 1726183Notes

Reaction equation

C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[N:32])[CH:26]=2)[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.O=[C:34]([CH3:48])[CH2:35][CH2:36][N:37]1C(=O)C2C(=CC=CC=2)C1=O>>[NH2:37][CH2:36][CH2:35][CH:34]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:24][C:25]2[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=2)[C:31]#[N:32])[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:23])=[O:22])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)[CH3:48]

Participants

Reactant 2

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

HCID 68972697HCID 68972697, compound

Product 1

HCID 68970630HCID 68970630, compound

Procedure

Using general procedure C with 4-[(3-cyano-benzyl)-(4-methanesulfinyl-phenyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (260 mg, 0.57 mmol), then general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (270 mg, 1.2 mmol) followed by general procedure D afforded 3-{[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(4-methanesulfinyl-phenyl)-amino]-methyl}-benzonitrile as a white solid (133 mg, 55% over 3 steps).

Sources & evidence

ORD record: ord-0e403a7db5f843d3bbbaa451261f2833
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

Loading…