3-Pyridinemethanamine → HCID 57920016, compound

HRID 555009Notes

Reaction equation

HRID 555009 reaction equation
NCC1C=NC=CC=1.[O:9]1[CH:13]=[CH:12][N:11]=[C:10]1[CH2:14][NH2:15].[F:16][C:17]1([F:36])[CH2:19][CH:18]1[CH2:20][N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32](O)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35]>>[F:36][C:17]1([F:16])[CH2:19][CH:18]1[CH2:20][N:21]1[CH2:25][CH2:24][N:23]([C:26]2[S:27][C:28]([C:32]([NH:15][CH2:14][C:10]3[O:9][CH:13]=[CH:12][N:11]=3)=[O:33])=[C:29]([CH3:31])[N:30]=2)[C:22]1=[O:35]

Participants

4

Reactant 3

HCID 310183-PyridinemethanamineHCID 18947655Oxazol-2-ylmethanamineHCID 579198122-(3-((2,2-Difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 57920016HCID 57920016, compoundYield 69%

Procedure

Following the procedure as describe in Example 16, making variations as required to replace 3-(aminomethyl)pyridine with (oxazol-2-yl)methylamine to react with 2-(3-((2,2-difluorocyclopropyl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid, the title compound was obtained as a colourless solid in 69% yield: mp 156-158° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.55 (t, J=5.7 Hz, 1H), 8.09 (s, 1H), 7.12 (s, 1H), 4.44 (d, J=5.7 Hz, 2H), 3.99 (t, J=8.4 Hz, 2H), 3.64-3.47 (m, 3H), 3.19-3.12 (m, 1H), 2.44 (s, 3H), 2.05-1.89 (m, 1H), 1.68-1.55 (m, 1H), 1.37-1.36 (m, 1H); 13C NMR (75 MHz, DMSO-d6) δ 163.8, 163.1, 159.5, 156.8, 153.4, 141.5, 128.9, 119.2, 43.9, 43.6, 42.6, 42.6, 38.4, 21.8 5 (t, 1JC-F=42 Hz), 19.0, 16.4 5 (t, 1JC-F=42 Hz); MS (ES+) m/z 399.0 (M+1).

Sources & evidence

ORD record
ord-721e9633cddf47eba6501eca61953914
Source dataset
uspto-grants-2011_11
Patent number
US08049016B2

Reaction notes

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