2-Fluorobenzoyl chloride → HCID 67153844, compound

HRID 714329Notes

Reaction equation

FC1C=CC=CC=1C(Cl)=O.[CH:11]1([CH2:14][C:15](Cl)=[O:16])[CH2:13][CH2:12]1.[NH2:18][C:19]1[CH:20]=[C:21]([CH:32]=[CH:33][N:34]=1)[C:22]([NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23]>>[CH2:25]([NH:24][C:22](=[O:23])[C:21]1[CH:32]=[CH:33][N:34]=[C:19]([NH:18][C:15](=[O:16])[CH2:14][CH:11]2[CH2:13][CH2:12]2)[CH:20]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

Reactant 3

HCID 98082-Fluorobenzoyl chloride

HCID 143262682-Cyclopropylacetyl chloride

HCID 187528972-amino-N-benzylisonicotinamide

Product 1

HCID 67153844HCID 67153844, compoundYield 57%

Procedure

Following the procedure as describe in Example 6, making variations as required to replace 2-fluorobenzoyl chloride with 2-cyclopropylacetyl chloride to react with 2-amino-N-benzylisonicotinamide, N-benzyl-2-(2-cyclopropylacetamido)isonicotinamide was obtained as a colorless solid in 57% yield: 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.48 (s, 1H), 8.34 (d, J=5.1 Hz, 1H), 7.53 (dd, J=5.1, 1.4 Hz, 1H), 7.31-7.24 (m, 5H), 6.87 (br s, 1H), 4.60 (d, J=5.8 Hz, 2H), 2.31 (d, J=7.2 Hz, 2H), 1.08-0.99 (m, 1H), 0.70-0.62 (m, 2H), 0.25 (q, J=4.9 Hz, 2H); MS (ES+) m/z 310.6 (M+1).

Sources & evidence

ORD record: ord-7bfc2cee2d6b45098363a9359e89771c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187426B2

Reaction notes

Loading…