HCID 55283830, compound → HCID 59481273, compound

HRID 560675Notes

Reaction equation

HRID 560675 reaction equation
C(N1CCN(C2SC(C(O)=O)=C(C)N=2)C1=O)C1C=CC=CC=1.[F:23][C:24]1[CH:45]=[CH:44][C:27]([CH2:28][N:29]2[CH2:33][CH2:32][N:31]([C:34]3[S:35][C:36]([C:40](O)=[O:41])=[C:37]([CH3:39])[N:38]=3)[C:30]2=[O:43])=[CH:26][CH:25]=1.[F:46][CH:47]([F:55])[C:48]1[O:52][C:51]([CH2:53][NH2:54])=[CH:50][CH:49]=1>>[F:46][CH:47]([F:55])[C:48]1[O:52][C:51]([CH2:53][NH:54][C:40]([C:36]2[S:35][C:34]([N:31]3[CH2:32][CH2:33][N:29]([CH2:28][C:27]4[CH:26]=[CH:25][C:24]([F:23])=[CH:45][CH:44]=4)[C:30]3=[O:43])=[N:38][C:37]=2[CH3:39])=[O:41])=[CH:50][CH:49]=1

Participants

4

Reactant 3

HCID 55283830HCID 55283830, compoundHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 579198662-(3-Benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 59481273HCID 59481273, compoundYield 47%

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 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid to react with (5-(difluoromethyl)furan-2-yl)methylamine, the title compound was obtained as a white powder in 47% yield: mp 173-174° C. (diethyl ether): 1H NMR (300 MHz, CDCl3) δ 7.28-7.22 (m, 2H), 7.05-6.99 (m, 2H), 6.59-6.56 (m, 1H), 6.55 (t, JH-F=54.4 Hz, 1H), 6.32-6.29 (m, 1H), 6.01 (t, J=5.4 Hz, 1H), 4.56 (d, J=5.4 Hz, 2H), 4.43 (s, 2H), 4.08-4.02 (m, 2H), 3.46-3.40 (m, 2H), 2.58 (s, 3H): 13C NMR (75 MHz, CDCl3) δ 164.2, 162.3, 160.9, 157.5, 155.4, 153.6, 153.3, 146.2, 130.3, 116.9, 115.8, 111.3, 108.4, 105.3, 47.3, 42.0, 41.7, 36.6, 17.3: MS (ES+) m/z 465.3 (M+1).

Sources & evidence

ORD record
ord-b0033f5280ab4e40ae250bd43e2542e0
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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