Aniline → HCID 25095672, compound

HRID 560661Notes

Reaction equation

HRID 560661 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][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=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:47])([F:46])[F:48])=[CH:42][CH:43]=3)[C:33]2=[O:49])[S:27][C:28]=1[C:29]([NH:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)=[O:30]

Participants

4

Reactant 3

HCID 6115AnilineHCID 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 25095672HCID 25095672, compoundYield 67%

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 aniline, the title compound was obtained as a white powder in 67% yield: mp 187-188° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.54 (d, J=6.0 Hz, 2H), 7.42 (br s, 1H), 7.36-7.28 (m, 4H), 7.19 (d, J=6.0 Hz, 2H), 7.15-7.08 (m, 1H), 4.47 (s, 2H), 4.12-4.07 (m, 2H), 3.50-3.44 (m, 2H), 2.63 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 160.6, 157.3, 155.4, 154.1, 149.0, 137.8, 134.3, 129.7, 129.0, 124.4, 121.4, 120.3, 120.2, 117.5, 47.3, 42.0, 41.8, 17.3; MS (ES+) m/z 477.3 (M+1).

Sources & evidence

ORD record
ord-e5fced409d6e4696a5ed96ea5848574a
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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