3-Pyridinemethanamine → HCID 59481294, compound

HRID 2067593Notes

Reaction equation

[NH2:1][CH2:2]C1C=NC=CC=1.Cl.[O:10]1[CH:14]=[CH:13][N:12]=[C:11]1NC.[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[C:27](=[O:28])[N:26]([C:29]3[S:33][C:32]([C:34]([OH:36])=O)=[C:31]([CH3:37])[CH:30]=3)[CH:25]=[N:24]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[C:27](=[O:28])[N:26]([C:29]3[S:33][C:32]([C:34]([NH:1][CH2:2][C:11]4[O:10][CH:14]=[CH:13][N:12]=4)=[O:36])=[C:31]([CH3:37])[CH:30]=3)[CH:25]=[N:24]2)=[CH:20][CH:19]=1

Participants

Reactant 3

HCID 310183-Pyridinemethanamine

HCID 53408680HCID 53408680, compound

HCID 594811895-(1-(4-fluorobenzyl)-5-oxo-1H-1,2,4-triazol-4(5H)-yl)-3-methylthiophene-2-carboxylic acid

Product 1

HCID 59481294HCID 59481294, compoundYield 50%

Procedure

Following the procedure as described in Example 31, making variations as required to replace 3-(aminomethyl)pyridine with oxazol-2-yl-methylamine hydrochloride 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 50% yield: mp 163-165° C.; 1H NMR (300 MHz, CDCl3) δ 7.72 (s, 1H), 7.64 (s, 1H), 7.40-7.34 (m, 2H), 7.08 (s, 1H), 7.06-6.99 (m, 2H), 6.91 (s, 1H), 6.64 (br s, 1H), 4.96 (s, 2H), 4.72 (d, J=5.2 Hz, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6 (d, JC-F=247.0 Hz), 162.3, 150.4, 140.6, 139.3, 135.0, 132.3, 131.2 (d, JC-F=3.3 Hz), 130.3 (d, JC-F=8.3 Hz), 127.1, 125.4, 120.4, 115.7 (d, JC-F=21.6 Hz), 48.9, 37.3, 16.0; MS (ES+) m/z 414.1 (M+1).

Sources & evidence

ORD record: ord-c72b01c844f24503a12d3eefbf7704aa
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08293768B2

Reaction notes

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