3-Pyridinemethanamine → HCID 24985446, compound

HRID 1887263Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][NH2:8])[CH:2]=1.[CH:9]1([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][N:18]([C:21]3[S:22][C:23]([C:27](O)=[O:28])=[C:24]([CH3:26])[N:25]=3)[C:17](=[O:30])[CH:16]=2)[CH2:11][CH2:10]1>>[CH:9]1([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][N:18]([C:21]3[S:22][C:23]([C:27]([NH:8][CH2:7][C:3]4[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=4)=[O:28])=[C:24]([CH3:26])[N:25]=3)[C:17](=[O:30])[CH:16]=2)[CH2:11][CH2:10]1

Participants

Reactant 2

HCID 310183-Pyridinemethanamine

HCID 24986107HCID 24986107, compound

Product 1

HCID 24985446HCID 24985446, compoundYield 47%

Procedure

Following the procedure as described in Example 1, making variations only as required to use pyridin-3-ylmethanamine in place of benzylamine to react with 2-(4-(2-cyclopropylethoxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 47% yield: mp 170-172° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 8.63 (d, J=8.1 Hz, 2H), 8.55 (s, 1H), 7.77 (d, J=7.8 Hz, 1H), 7.37-7.27 (m, 1H), 6.43 (t, J=5.7 Hz, 1H), 6.16 (dd, J=8.1, 2.6 Hz, 1H), 5.96 (d, J=2.6 Hz, 1H), 4.62 (d, J=5.7 Hz, 2H), 4.03 (t, J=6.6 Hz, 2H), 2.67 (s, 3H), 1.68 (q, J=6.6 Hz, 2H), 0.86-0.74 (m, 1H), 0.52-0.46 (m, 2H), 0.13-0.08 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 167.9, 162.5, 162.1, 153.7, 152.6, 148.6, 148.3, 136.3, 131.3, 121.7, 104.2, 96.6, 69.1, 41.4, 33.6, 17.3, 7.56, 4.2; MS (ES+) m/z 411.2 (M+1).

Sources & evidence

ORD record: ord-9f77ad52102f4ade90b4ba162e63863e
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501746B2

Reaction notes

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