2-(Pyridin-3-yl)ethan-1-amine → HCID 59481248, compound

HRID 560663Notes

Reaction equation

HRID 560663 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][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=3)[C:33]2=[O:49])[S:27][C:28]=1[C:29](O)=[O:30].[NH2:50][CH2:51][CH2:52][C:53]1[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=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:39]=[CH:40][C:41]([O:44][C:45]([F:46])([F:47])[F:48])=[CH:42][CH:43]=3)[C:33]2=[O:49])[S:27][C:28]=1[C:29]([NH:50][CH2:51][CH2:52][C:53]1[CH:54]=[N:55][CH:56]=[CH:57][CH:58]=1)=[O:30]

Participants

4

Reactant 3

HCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 594812844-Methyl-2-(2-oxo-3-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid

Product 1

HCID 59481248HCID 59481248, compoundYield 21%

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-(4-(trifluoromethoxy)benzyl)imidazolidin-1-yl)thiazole-5-carboxylic acid to react with 3-(2-aminoethyl)pyridine, the title compound was obtained as a white powder in 21% yield: mp 172-173° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 8.46 (s, 2H), 7.53 (d, J=7.8 Hz, 1H), 7.35-7.16 (m, 5H), 5.81 (br s, 1H), 4.46 (s, 2H), 4.08-4.03 (m, 2H), 3.65-3.59 (m, 2H), 3.47-3.42 (m, 2H), 2.92-2.87 (m, 2H), 2.53 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 162.6, 157.2, 155.4, 152.8, 150.1, 148.9, 148.1, 136.2, 134.3, 134.2, 129.6, 123.5, 121.4, 117.5, 47.2, 42.0, 41.8, 40.9, 33.0, 17.1; MS (ES+) m/z 506.4 (M+1).

Sources & evidence

ORD record
ord-60d2c39fc956451cb0bb9c808e859a58
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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