3,5-Dichloro-2-pyridinecarboxylic acid → (E)-3,5-Dichloro-N-(8-(hydroxymethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide

HRID 1911045Notes

Reaction equation

HRID 1911045 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.[Cl:16][C:17]1[C:18]([C:24](O)=[O:25])=[N:19][CH:20]=[C:21]([Cl:23])[CH:22]=1>>[Cl:16][C:17]1[C:18]([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:19][CH:20]=[C:21]([Cl:23])[CH:22]=1

Participants

3

Reactant 2

HCID 2199893,5-Dichloro-2-pyridinecarboxylic acidHCID 86685427(2-amino-9-methyl-6,7-dihydro-5H-benzo[7]annulen-8-yl)methanol

Product 1

HCID 86685436(E)-3,5-Dichloro-N-(8-(hydroxymethyl)-9-methyl-6,7-dihydro-5H-benzo[7]annulen-2-yl)picolinamide

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 3,5-dichloropicolinic acid to afford the titled compound of Step 45A. LCMS (M+H)+=375.2. 1H NMR (500 HMz, methanol-d4) δ 8.62 (d, J=2.0 Hz, 1H), 8.18 (d, J=2.1 Hz, 1H), 7.65 (d, J=2.1 Hz, 1H), 7.50 (dd, J=8.1, 2.3 Hz, 1H), 7.19 (d, J=8.2 Hz, 1H), 4.33 (s, 2H), 2.56 (t, J=7.0 Hz, 2H), 2.14 (s, 3H), 2.13-2.08 (m, 2H), 2.00-1.95 (m, 2H).

Sources & evidence

ORD record
ord-55159d4d60b44363b82c360dcccaf1dc
Source dataset
uspto-grants-2013_12
Patent number
US08604024B2

Reaction notes

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