3-Pyridinemethanamine → HCID 24958967, compound

HRID 2381845Notes

Reaction equation

HRID 2381845 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[CH:14]=[C:13]([CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20]C=3)[N:12]=[N:11]2)[S:5][C:6]=1[C:7]([OH:9])=O.CC1N=C(N2C=C(CC(C3C=CC=CC=3)C)N=N2)SC=1C(O)=O.[N:47]1[CH:52]=[CH:51][CH:50]=[C:49]([CH2:53][NH2:54])[CH:48]=1>>[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[CH:14]=[C:13]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:23][CH:22]=[CH:21][CH:20]=3)[N:12]=[N:11]2)[S:5][C:6]=1[C:7]([NH:54][CH2:53][C:49]1[CH:48]=[N:47][CH:52]=[CH:51][CH:50]=1)=[O:9]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 59179706HCID 59179706, compoundHCID 68494698HCID 68494698, compound

Product 1

HCID 24958967HCID 24958967, compoundYield 25%

Procedure

Following the procedure as described in Example 14, making variations as necessary to replace 4-methyl-2-(4-(3-phenylpropyl)-1H-1,2,3-triazol-1-yl)thiazole-5-carboxylic acid with 4-methyl-2-(4-(2-phenylpropyl)-1H-1,2,3-triazol-1-yl)thiazole-5-carboxylic acid to react with pyridin-3-ylmethanamine, the title compound was obtained as a white solid in 25% yield: mp 114-116° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.59-8.53 (m, 2H), 8.02 (s, 1H), 7.75-7.72 (m, 1H), 7.33-7.18 (m, 6H), 5.57 (m, 1H), 4.64 (d, J=5.9 Hz, 2H), 3.13-3.02 (m, 4H), 2.67 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 161.2, 155.7, 153.9, 149.0, 148.9, 148.6, 140.5, 135.9, 133.6, 128.5, 128.4, 126.3, 123.8, 123.4, 118.6, 41.7, 35.0, 27.2, 17.5; MS (ES+) m/z 405.1 (M+1).

Sources & evidence

ORD record
ord-c400e48f7aa8412eaa07e4342614271e
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

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