3-Pyridinemethanamine → HCID 57919816, compound

HRID 554983Notes

Reaction equation

HRID 554983 reaction equation
F[C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[N:6][CH:7]=1.N1C=CC=C(CN)C=1.[CH3:18][C:19]1[N:20]=[C:21]([N:27]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][C:35]([F:38])([F:37])[F:36])[C:28]2=[O:39])[S:22][C:23]=1[C:24](O)=[O:25]>>[CH3:18][C:19]1[N:20]=[C:21]([N:27]2[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][CH2:34][C:35]([F:36])([F:37])[F:38])[C:28]2=[O:39])[S:22][C:23]=1[C:24]([NH:9][CH2:8][C:4]1[CH:5]=[N:6][CH:7]=[CH:2][CH:3]=1)=[O:25]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198994-Methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 57919816HCID 57919816, compoundYield 50%

Procedure

Following the procedure as describe in Example 12, making variations as required to replace (5-fluoropyridin-3-yl)methanamine with pyridin-3-ylmethanamine to react with 4-methyl-2-(2-oxo-3-(4,4,4-trifluorobutyl)imidazolidin-1-yl)thiazole-5-carboxylic acid in place of 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colorless solid in 50% yield: mp 167-169° C. (dichloromethane/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.62-8.52 (m, 2H), 7.69-7.66 (m, 1H), 7.26-7.24 (m, 1H), 6.28-6.25 (m, 1H), 4.57 (d, J=5.9 Hz, 2H), 4.14-4.09 (m, 2H), 3.62-3.56 (m, 2H), 3.40-3.36 (m, 2H), 2.60 (s, 3H), 2.18-2.09 (m, 2H), 1.89-1.79 (m, 2H); MS (ES+) m/z 428.1 (M+1).

Sources & evidence

ORD record
ord-5bcbb172a9a940ffbde6ce9d7ea5d8c8
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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