3-Pyridinemethanamine → HCID 59481251, compound

HRID 560815Notes

Reaction equation

HRID 560815 reaction equation
NCC1C=NC=CC=1.[NH2:9][CH2:10][C:11]1[CH:16]=[N:15][C:14]([CH3:17])=[CH:13][N:12]=1.[F:18][C:19]1[CH:40]=[CH:39][C:22]([CH2:23][N:24]2[C:28](=[O:29])[N:27]([C:30]3[S:34][C:33]([C:35](O)=[O:36])=[C:32]([CH3:38])[CH:31]=3)[CH:26]=[N:25]2)=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:40]=[CH:39][C:22]([CH2:23][N:24]2[C:28](=[O:29])[N:27]([C:30]3[S:34][C:33]([C:35]([NH:9][CH2:10][C:11]4[CH:16]=[N:15][C:14]([CH3:17])=[CH:13][N:12]=4)=[O:36])=[C:32]([CH3:38])[CH:31]=3)[CH:26]=[N:25]2)=[CH:21][CH:20]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 27564962-(Aminomethyl)-5-methylpyrazineHCID 594811895-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 59481251HCID 59481251, compoundYield 76%

Procedure

Following the procedure as described in Example 31, making variations as required to replace 3-(aminomethyl)pyridine with 2-(aminomethyl)-5-methylpyrazine to react with 5-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid, the title compound was obtained as a colorless solid in 76% yield: mp 189-191° C.; 1H NMR (300 MHz, CDCl3) δ 8.52 (s, 1H), 8.40 (s, 1H), 7.72 (s, 1H), 7.41-7.34 (m, 2H), 7.07-6.99 (m, 2H), 6.98 (t, J=4.7 Hz, 1H), 6.92 (s, 1H), 4.96 (s, 2H), 4.71 (d, J=4.7 Hz, 2H), 2.56 (s, 3H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6 (d, JC-F=246.9 Hz), 162.4, 152.7, 150.4, 148.4, 143.4, 142.8, 140.1, 134.8, 132.4, 131.2 (d, JC-F=3.2 Hz), 130.3 (d, JC-F=8.3 Hz), 126.1, 120.5, 115.7 (d, JC-F=21.7 Hz), 49.0, 42.3, 21.2, 16.0; MS (ES+) m/z 439.2 (M+1).

Sources & evidence

ORD record
ord-e09897329cdf438c9303f2626bfdab02
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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