5-Cyanopyridine-2-carboxylic acid → (E)-5-Cyano-N-(8-(hydroxymethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:11][CH2:10][CH2:9][C:8]([CH2:12][OH:13])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[C:16]([C:18]1[CH:19]=[CH:20][C:21]([C:24](O)=[O:25])=[N:22][CH:23]=1)#[N:17]>>[C:16]([C:18]1[CH:19]=[CH:20][C:21]([C:24]([NH:1][C:2]2[CH:3]=[CH:4][C:5]3[CH2:11][CH2:10][CH2:9][C:8]([CH2:12][OH:13])=[C:7]([CH3:14])[C:6]=3[CH:15]=2)=[O:25])=[N:22][CH:23]=1)#[N:17]Participants
3
Procedure
In a manner similar to the procedure of step 3A, (E)-(2-amino-9-methyl-6,7-dihydro-5H-benzo[7]annulen-8-yl)methanol from preparation J was coupled with 5-cyanopicolinic acid to afford the titled compound of Step 44A. 1H NMR (500 HMz, chloroform-d) δ 9.84 (s, 1H), 8.90 (dd, J=2.0, 0.8 Hz, 1H), 8.45 (dd, J=8.1, 0.8 Hz, 1H), 8.21 (dd, J=8.1, 2.0 Hz, 1H), 7.68 (d, J=2.3 Hz, 1H), 7.56 (dd, J=8.1, 2.3 Hz, 1H), 7.21 (d, J=8.2 Hz, 1H), 4.41 (s, 2H), 2.56 (t, J=7.0 Hz, 2H), 2.16 (s, 3H), 2.12 (quin, J=7.1 Hz, 2H), 2.02-1.96 (m, 2H), 1.57 (br. s., 1H).
Sources & evidence
- ORD record
- ord-ff930acdd2ea449ab219ff6c6126230a
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604024B2
Reaction notes
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