Diisopropylethylamine → {4-[(3,4-Dimethoxy-pyridin-2-ylmethyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

HRID 1592449Notes

Reaction equation

HRID 1592449 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:23][O:24][C:25]1[C:26]([CH2:33]Cl)=[NH+:27][CH:28]=[CH:29][C:30]=1[O:31][CH3:32].[CH3:35]CN(C(C)C)C(C)C>CC#N>[C:1]([O:5][C:6](=[O:21])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:33][C:26]1[C:25]([O:24][CH3:23])=[C:30]([O:31][CH3:32])[CH:29]=[CH:28][N:27]=1)[CH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([CH3:35])=[CH:16][N:15]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 534236922-Chloromethyl-3,4-dimethoxypyridinium hydrochlorideHCID 58997087{4-[(3-Methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

Product 1

HCID 67271982{4-[(3,4-Dimethoxy-pyridin-2-ylmethyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Using General Procedure A: Reaction of {4-[(3-methyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester, 3,4-dimethoxy-2-chloromethylpyridinium hydrochloride, DIPEA and KI in CH3CN gave {4-[(3,4-dimethoxy-pyridin-2-ylmethyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-butyl}-carbamic acid tert-butyl ester as an oily residue. 1H NMR (CDCl3) δ 1.30-1.35 (m, 2H), 1.43 (s, 9H), 1.48-1.55(m, 2H), 2.14 (s, 3H), 2.27 (s, 3H), 2.95-3.00 (m, 2H), 3.76 (s, 6H), 3.91 (s, 3H), 5.14 (bs, 1H), 6.79 (d, 1H, J=6.9 Hz), 7.22 (s, 1H), 8.19 (s, 1H), 8.25 (d, 1H, J=6.9 Hz).

Sources & evidence

ORD record
ord-0d6c5b2351bb4011a9ff7ea369ff899f
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

Loading…