2-Pyridinemethanamine → HCID 57919882, compound

HRID 554969Notes

Reaction equation

N1C=CC=C(CN)C=1.[N:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][NH2:16].FC1C=CC(CN2[C@@H](C)CN(C3SC(C(O)=O)=C(C)N=3)C2=O)=CC=1.[CH3:41][C:42]1[N:43]=[C:44]([N:50]2[CH2:54][C@@H:53]([CH3:55])[N:52]([CH2:56][C:57]3[CH:62]=[CH:61][C:60]([C:63]([F:66])([F:65])[F:64])=[CH:59][CH:58]=3)[C:51]2=[O:67])[S:45][C:46]=1[C:47](O)=[O:48]>>[CH3:41][C:42]1[N:43]=[C:44]([N:50]2[CH2:54][C@@H:53]([CH3:55])[N:52]([CH2:56][C:57]3[CH:62]=[CH:61][C:60]([C:63]([F:64])([F:66])[F:65])=[CH:59][CH:58]=3)[C:51]2=[O:67])[S:45][C:46]=1[C:47]([NH:16][CH2:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][N:9]=1)=[O:48]

Participants

Reactant 4

HCID 195092-Pyridinemethanamine

HCID 310183-Pyridinemethanamine

HCID 57919976(S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

HCID 66661603HCID 66661603, compound

Product 1

HCID 57919882HCID 57919882, compound

Procedure

Following the procedure as described in Example 2, making variations as required to replace pyridin-3-ylmethanamine with pyridin-2-ylmethanamine and replace (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid with (R)-4-methyl-2-(4-methyl-2-oxo-3-(4-(trifluoromethyl)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid, the title compound was obtained as a solid (61%): mp 136-137° C. (ethyl acetate/hexane); 1H NMR (300 MHz, DMSO-d6) δ 8.55-8.49 (m, 2H), 7.79-7.71 (m, 3H), 7.56 (d, J=8.1 Hz, 2H), 7.31-7.24 (m, 2H), 4.67 (d, J=16.1 Hz, 1H), 4.49-4.43 (m, 3H), 4.22 (dd, J=10.1, 9.1 Hz, 1H), 3.84-3.77 (m, 1H), 3.56 (dd, J=10.1, 6.8 Hz, 1H), 2.49 (s, 3H), 1.22 (d, J=6.2 Hz, 3H); MS (ES+) m/z 489.9 (M+1).

Sources & evidence

ORD record: ord-99c76aaa0e854787a1dbaada695b699e
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049016B2

Reaction notes

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