3-Pyridinemethanamine → HCID 25095153, compound

HRID 560726Notes

Reaction equation

HRID 560726 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([N:7]2[CH2:11][CH2:10][N:9]([CH2:12][C:13]3[CH:18]=[CH:17][C:16](C(F)(F)F)=[CH:15][CH:14]=3)[C:8]2=[O:23])[S:4][C:3]=1[C:24](O)=[O:25].C(N1CCN(C2SC(C(O)=O)=C(C)C=2)C1=O)C1C=CC=CC=1.[NH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1>>[CH2:12]([N:9]1[CH2:10][CH2:11][N:7]([C:5]2[S:4][C:3]([C:24]([NH:49][CH2:50][C:51]3[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=3)=[O:25])=[C:2]([CH3:1])[CH:6]=2)[C:8]1=[O:23])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 580315465-(3-Benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acidHCID 580315813-Methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylic acid

Product 1

HCID 25095153HCID 25095153, compoundYield 46%

Procedure

Following the procedure as described in Example 15, making variations as required to replace 3-methyl-5-(2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiophene-2-carboxylic acid with 5-(3-benzyl-2-oxoimidazolidin-1-yl)-3-methylthiophene-2-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a colorless solid in 46% yield: mp 130-131° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.51 (s, 1H), 7.69 (d, J=7.8 Hz, 1H), 7.38-7.22 (m, 6H), 6.18 (t, J=5.6 Hz, 1H), 6.07 (s, 1H), 4.58 (d, J=5.6 Hz, 2H), 4.44 (s, 2H), 3.81-3.74 (m, 2H), 3.47-3.40 (m, 2H), 2.48 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 163.5, 155.9, 149.2, 148.8, 142.6, 141.8, 135.9, 135.5, 128.8, 128.2, 127.9, 123.6, 118.9, 112.3, 48.1, 42.7, 41.5, 41.2, 16.1; MS (ES+) m/z 407.3 (M+1).

Sources & evidence

ORD record
ord-cf722b7f225743e993173af2a210523e
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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