2-(3-Oxobutyl)isoindoline-1,3-dione → HCID 68971422, compound

HRID 1726131Notes

Reaction equation

HRID 1726131 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]([C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=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[CH2:9][CH2:10][CH:11]([CH:14]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH3:22])[N:17]=2)[C:23]2[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=2)[CH2:12][CH2:13]1)[CH3:46]

Participants

3

Reactant 2

HCID 2907282-(3-Oxobutyl)isoindoline-1,3-dioneHCID 68970352HCID 68970352, compound

Product 1

HCID 68971422HCID 68971422, compoundYield 44.8%

Procedure

Using general procedure C with the above carbamate (1.2 g, 2.95 mmol), then general procedure B with the resulting amine and 2-(3-oxo-butyl)-isoindole-1,3-dione (1.2 g, 5.60 mmol) followed by general procedure D afforded 4-[[1-(3-amino-1-methyl-propyl)-piperidin-4-yl]-(6-methyl-pyridin-2-yloxy)-methyl]-benzonitrile (500 mg, 40% over 4 steps) as a white foam.

Sources & evidence

ORD record
ord-929af957e43f4fa1b32cb9ff20dae50d
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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