3-Pyridinemethanamine → HCID 59481274, compound

HRID 560674Notes

Reaction equation

C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[CH3:23][C:24]1[N:25]=[C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:47])([F:46])[F:45])[CH:39]=3)[C:33]2=[O:48])[S:27][C:28]=1[C:29]([OH:31])=O.[NH2:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1>>[CH3:23][C:24]1[N:25]=[C:26]([N:32]2[CH2:36][CH2:35][N:34]([CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([C:44]([F:45])([F:46])[F:47])[CH:39]=3)[C:33]2=[O:48])[S:27][C:28]=1[C:29]([NH:49][CH2:50][C:51]1[CH:52]=[N:53][CH:54]=[CH:55][CH:56]=1)=[O:31]

Participants

Reactant 3

HCID 310183-Pyridinemethanamine

HCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HCID 58031468HCID 58031468, compound

Product 1

HCID 59481274HCID 59481274, compoundYield 81%

Procedure

Following the procedure as describe in Example 9, making variations as required to replace 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with 4-methyl-2-(2-oxo-3-(3-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(aminomethyl)pyridine, the title compound was obtained as a white powder in 81% yield: mp 175-176° C. (diethyl ether); 1H NMR (300 MHz, CDCl3) 8.58 (s, 1H), 8.50 (d, J=4.8 Hz, 1H), 7.67 (d, J=7.8 Hz, 1H), 7.61-7.54 (m, 1H), 7.53-7.44 (m, 3H), 7.29-7.21 (m, 1H), 6.21 (t, J=5.6 Hz, 1H), 4.57 (d, J=5.6 Hz, 2H), 4.51 (s, 2H), 4.14-4.02 (m, 2H), 3.52-3.41 (m, 2H), 2.59 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.2, 155.5, 153.7, 149.3, 149.0, 136.7, 135.6, 133.9, 131.6, 131.5, 131.1, 129.5, 125.0, 124.9, 123.6, 117.1, 47.7, 42.0, 41.9, 41.4, 17.3; MS (ES+) m/z 476.4 (M+1).

Sources & evidence

ORD record: ord-d49cc20ffdb74f56b8f39dab4deac625
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063084B2

Reaction notes

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