2-Fluorobenzoyl chloride → HCID 67153862, compound

HRID 714324Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[C:11]1([C:21](Cl)=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.[NH2:24][C:25]1[CH:26]=[C:27]([CH:38]=[CH:39][N:40]=1)[C:28]([NH:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29]>>[C:11]1([C:21]([NH:24][C:25]2[CH:26]=[C:27]([CH:38]=[CH:39][N:40]=2)[C:28]([NH:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

Reactant 3

HCID 98082-Fluorobenzoyl chloride

HCID 701461-Naphthalenecarbonyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153862HCID 67153862, compoundYield 20%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 1-naphthoyl chloride to react with 2-amino-N-benzylisonicotinamide, 2-(1-naphthamido)-N-benzylisonicotinamide was obtained as a colorless solid in 20% yield: mp 65-67° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 9.70 (s, 1H), 8.72 (s, 1H), 8.29-8.22 (m, 1H), 7.95 (d, J=8.3 Hz, 1H), 7.97-7.84 (m, 1H), 7.76 (d, J=5.2 Hz, 1H), 7.69 (d, J=5.2 Hz, 1H), 7.50-7.31 (m, 7H), 7.28-7.24 (m, 2H), 7.08 (t, J=5.8 Hz, 1H), 4.59 (d, J=5.7 Hz, 2H); MS (ES+) m/z 382.5 (M+1).

Sources & evidence

ORD record: ord-33835e9c0d374f2287da06302dda1bf1
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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