2-Fluorobenzoyl chloride → HCID 67153875, compound

HRID 714320Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16](Cl)=[O:17].[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]([C:12]2[S:11][CH:15]=[CH:14][CH:13]=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 789282-Thiophenecarbonyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153875HCID 67153875, compoundYield 73%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with thiophene-2-carbonyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(thiophene-2-carboxamido)isonicotinamide was obtained as a colorless solid in 73% yield: mp 160-162° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 11.07 (s, 1H), 9.32 (t, J=5.7 Hz, 1H), 8.53-8.47 (m, 2H), 8.23-8.22 (m, 1H), 7.87 (d, J=5.0 Hz, 1H), 7.58-7.48 (m, 1H), 7.31-7.37 (m, 6H), 4.46 (d, J=5.9 Hz, 2H); MS (ES+) m/z 338.5 (M+1).

Sources & evidence

ORD record: ord-d0fe7bee96234ac39d61a9db86b4168a
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

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