2-Fluorobenzoyl chloride → HCID 67153872, compound

HRID 714330Notes

Reaction equation

HRID 714330 reaction equation
FC1C=CC=CC=1C(Cl)=O.[CH3:11][S:12]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][CH:23]=1)[C:18](Cl)=[O:19])(=[O:14])=[O:13].[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]>>[CH2:31]([NH:30][C:28](=[O:29])[C:27]1[CH:38]=[CH:39][N:40]=[C:25]([NH:24][C:18](=[O:19])[C:17]2[CH:21]=[CH:22][CH:23]=[C:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH:16]=2)[CH:26]=1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 3

HCID 98082-Fluorobenzoyl chlorideHCID 187528972-amino-N-benzylisonicotinamideHCID 221378393-(Methanesulfonyl)benzoyl chloride

Product 1

HCID 67153872HCID 67153872, compoundYield 36%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 3-(methylsulfonyl)benzoyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(3-(methylsulfonyl)benzamido)-isonicotinamide was obtained as a colorless solid in 36% yield: mp 170-171° C. (hexanes/ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 11.33 (s, 1H), 9.34 (t, J=5.9 Hz, 1H), 8.58 (s, 1H), 8.52-8.50 (m, 2H), 8.30-8.27 (m, 1H), 8.11-8.08 (m, 1H), 7.80-7.75 (m, 1H), 7.56 (dd, J=5.2, 1.5 Hz, 1H), 7.34-7.19 (m, 5H), 4.47 (d, J=5.9 Hz, 2H), 3.26 (s, 3H); MS (ES+) m/z 410.5 (M+1).

Sources & evidence

ORD record
ord-0c422f3e5d6a4ccdafec07854e39b1a7
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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