Picolyl chloride → HCID 18422110, compound

HRID 1281713Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)=[O:17])[CH:11]=[CH:12][C:13]=1[CH3:14])=[O:6].Cl[CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1>>[N:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][O:1][C:2]1[CH:3]=[C:4]([CH:28]=[CH:29][CH:30]=1)[C:5]([NH:7][C:8]1[CH:9]=[C:10]([NH:15][C:16]([C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)=[O:17])[CH:11]=[CH:12][C:13]=1[CH3:14])=[O:6]

Participants

Reactant 2

HCID 23393Picolyl chloride

HCID 18422129HCID 18422129, compound

Product 1

HCID 18422110HCID 18422110, compoundYield 58%

Procedure

Using an analogous procedure to that described in Example 7, N-[3-(3-hydroxybenzamido)-4-methylphenyl]quinoline-6-carboxamide was reacted with 2-chloromethylpyridine to give the title compound in 58% yield; NMR Spectrum: (DMSOd6) 2.2 (s, 3H), 5.26 (s, 2H), 7.23 (m, 2H), 7.33 (t, 1H), 7.43 (t, 1H), 7.57 (t, 1H), 7.61 (m, 4H), 7.82 (m, 1H), 7.85 (d, 1H), 8.12 (d, 1H), 8.25 (d, 1H), 8.51 (d, 1H), 8.58 (d, 1H), 8.61 (s, 1H), 8.99 (d, 1H), 9.9 (s, 1H), 10.48 (s, 1H); Mass Spectrum: M+H+ 489.

Sources & evidence

ORD record: ord-66433e19b83648adbcf5882d79ee2ff4
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455520B1

Reaction notes

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