HCID 68328010, compound → HCID 90386028, compound

HRID 2274884Notes

Reaction equation

HRID 2274884 reaction equation
[CH2:1]=[C:2]([C:4]1[CH:5]=[C:6]([C:10]([NH:13][C:14]([N:16]2[CH:22]3[CH2:23][CH2:24][N:19]([CH2:20][CH2:21]3)[CH2:18][CH2:17]2)=[O:15])([CH3:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH3:3]>[Pd]>[CH3:3][CH:2]([C:4]1[CH:5]=[C:6]([C:10]([NH:13][C:14]([N:16]2[CH:22]3[CH2:21][CH2:20][N:19]([CH2:24][CH2:23]3)[CH2:18][CH2:17]2)=[O:15])([CH3:12])[CH3:11])[CH:7]=[CH:8][CH:9]=1)[CH3:1]

Participants

3

Reactant 1

HCID 68328010HCID 68328010, compound

Product 1

HCID 90386028HCID 90386028, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Using general procedure F, N-(2-(3-(prop-1-en-2-yl)phenyl)propan-2-yl)-1,4-diazabicyclo[3.2.2]nonane-4-carboxamide (100 mg, 0.305 mmol) and palladium, (20 mg, 20 wt. % on carbon) gave the title compound as an off-white solid (60 mg, 57%). 1H NMR (400 MHz, CDCl3) δ 7.28-7.21 (m, 3H), 7.11 (d, J=8.0 Hz, 1H), 4.71 (s, 1H), 4.02 (s, 1H), 3.66 (t, J=8.0 Hz, 2H) 3.15 (m, 7H), 2.06 (br s, 2H), 1.77 (s, 7H) 1.26 (d, J=4.0 Hz, 6H) ppm. 13C NMR (100 MHz, CDCl3) δ 155.8, 148.9, 148.5, 128.5.1, 124.7, 123.1, 122.4, 57.8, 56.0, 48.1, 46.4, 41.2, 34.5, 32.2, 30.4, 30.0, 29.9, 27.3, 24.3, 22.9 ppm. Purity: >91% UPLCMS (210 nm); retention time 0.74 min; (M+1) 330.

Sources & evidence

ORD record
ord-1abcf740e1e64d7c9f38a014d9bb50df
Source dataset
uspto-grants-2015_09
Patent number
US09126993B2

Reaction notes

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