4-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridine → HCID 22557903, compound

HRID 2300367Notes

Reaction equation

HRID 2300367 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:10][CH2:9][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]3[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=3)[CH:13]=2)[CH2:7][CH2:6]1)[C:2]#[CH:3].[Cl:30][CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([C:38]2[CH:43]=[C:42]([O:44][CH3:45])[C:41]([O:46][CH3:47])=[C:40]([O:48][CH3:49])[CH:39]=2)[CH:33]=1>>[ClH:30].[ClH:30].[ClH:30].[ClH:30].[CH2:1]([N:4]([CH:5]1[CH2:6][CH2:7][N:8]([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[C:14]([C:18]3[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=3)[CH:13]=2)[CH2:9][CH2:10]1)[CH2:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]([C:38]2[CH:43]=[C:42]([O:44][CH3:45])[C:41]([O:46][CH3:47])=[C:40]([O:48][CH3:49])[CH:39]=2)[CH:33]=1)[C:2]#[CH:3]

Participants

3

Reactant 2

HCID 120192374-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridineHCID 22557994HCID 22557994, compound

Product 1

HCID 22557903HCID 22557903, compound

Procedure

4-Propargylamino-1-[[2-(3,4,5-trimethoxyphenyl]pyridin-4-yl]methyl]piperidine (227 mg) and 4-chloromethyl-2-(3,4,5-trimethoxyphenyl)pyridine (226 mg) were condensed in the same manner as described in Example 9. The title compound was obtained as yellow powder after converting a free base to a tetrahydrochloride. Yield: 128 mg (23%). 1H-NMR (400 MHz, measured as a free base, CDCl3) δ: 1.48-2.40 (m, 7H), 2.72 (br, 1H), 3.02 (br, 2H), 3.39 (s, 2H), 3.64 (br, 2H), 3.84 (s, 2H), 3.91 (s, 6H), 3.98 (s, 6H), 3.99 (s, 6H), 7.22-7.29 (m, 6H), 7.66 (br, 2H), 8.60 (d, 1H, J=4.9 Hz), 8.62 (d, 1H, J=4.9 Hz).

Workup

  1. customcondensed in the same manner

Sources & evidence

ORD record
ord-e22e5b22196f471c9add9ff30682ef71
Source dataset
uspto-grants-2002_12
Patent number
US06498169B1

Reaction notes

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