Picolyl chloride → HCID 18422078, compound

HRID 1281717Notes

Reaction equation

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

Participants

Reactant 2

HCID 23393Picolyl chloride

HCID 18422118HCID 18422118, compound

Product 1

HCID 18422078HCID 18422078, compoundYield 72%

Conditions

Temperature: 40 °C

Procedure

Using an analogous procedure to that described in Example 7 except that the reaction mixture was heated to 70° C. for 48 hours rather than to 40° C. for 18 hours, N-[3-(4-hydroxybenzamido)-4-methylphenyl]quinoline-6-carboxamide was reacted with 2-chloromethylpyridine to give the title compound in 72% yield; NMR Spectrum: (DMSOd6) 2.22 (s, 3H), 5.28 (s, 2H), 7.16 (d, 2H), 7.22 (d, 1H), 7.34 (m, 1H), 7.53 (m, 1H), 7.62 (m, 2H), 7.85 (m, 2H), 7.95 (m, 1H), 8.12 (d, 1H), 8.23 (m, 1H), 8.52 (m, 1H), 8.59 (m, 2H), 9.0 (d, 1H), 10.48 (s, 1H); Mass Spectrum: M+H+ 489.

Sources & evidence

ORD record: ord-8354e0e9de0a45688c050a34d19f65c4
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455520B1

Reaction notes

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