2-Fluorobenzoyl chloride → HCID 67153855, compound

HRID 714319Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[CH:11]1([C:16](Cl)=[O:17])[CH2:15][CH2:14][CH2:13][CH2:12]1.[NH2:19][C:20]1[CH:21]=[C:22]([CH:33]=[CH:34][N:35]=1)[C:23]([NH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24]>>[CH2:26]([NH:25][C:23](=[O:24])[C:22]1[CH:33]=[CH:34][N:35]=[C:20]([NH:19][C:16]([CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:17])[CH:21]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Reactant 3

HCID 98082-Fluorobenzoyl chloride

HCID 78284Cyclopentanecarbonyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153855HCID 67153855, compoundYield 88%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with cyclopentanecarbonyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(cyclopentanecarboxamido)-isonicotinamide was obtained as a colorless solid in 88% yield: mp 55-57° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.91 (s, 1H), 8.49 (s, 1H), 8.27 (d, J=5.1 Hz, 1H), 7.49 (d, J=5.1 Hz, 1H), 7.23-7.18 (m, 6H), 4.54 (d, J=5.7 Hz, 2H), 2.82-2.80 (m, 1H), 1.22-0.82 (m, 8H); 13C NMR (75 MHz, CDCl3) δ 175.7, 165.3, 152.2, 148.2, 144.1, 137.5, 128.7, 128.4, 127.9, 127.6, 118.2, 110.9, 46.4, 44.1, 30.3, 25.9; MS (ES+) m/z 324.6 (M+1).

Sources & evidence

ORD record: ord-0e623e37ec0e4b6589a4a72db7e733f7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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