Oxazol-2-ylmethanamine → HCID 59481258, compound

HRID 560830Notes

Reaction equation

HRID 560830 reaction equation
ClC1C=CC2SC=C(CN3CCN(C4SC(C(O)=O)=C(C)N=4)C3=O)C=2C=1.[F:27][C:28]1[CH:49]=[CH:48][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:39][C:40]([C:44](O)=[O:45])=[C:41]([CH3:43])[N:42]=3)[C:34]2=[O:47])=[CH:30][CH:29]=1.[O:50]1[CH:54]=[CH:53][N:52]=[C:51]1[CH2:55][NH2:56]>>[F:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:32][N:33]2[CH2:37][CH2:36][N:35]([C:38]3[S:39][C:40]([C:44]([NH:56][CH2:55][C:51]4[O:50][CH:54]=[CH:53][N:52]=4)=[O:45])=[C:41]([CH3:43])[N:42]=3)[C:34]2=[O:47])=[CH:48][CH:49]=1

Participants

4

Reactant 3

HCID 18947655Oxazol-2-ylmethanamineHCID 579197992-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acidHCID 580315052-(3-((5-Chlorobenzo[b]thiophen-3-yl)methyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Product 1

HCID 59481258HCID 59481258, compoundYield 32%

Procedure

Following the procedure as described in Example 32, making variations as required to replace 2-(3-((5-chlorobenzo[b]thiophen-3-yl)methyl)-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 oxazol-2-ylmethanamine, the title compound was obtained as a colorless solid in 32% yield: mp 187-189° C.; 1H NMR (300 MHz, CDCl3) δ 7.65 (s, 1H), 7.30-7.27 (m, 2H), 7.09-7.02 (m, 3H), 6.35 (br s, 1H), 4.70 (d, J=3.0 Hz, 2H), 4.47 (s, 2H), 4.10 (t, J=9.0 Hz, 2H), 3.46 (t, J=9.0 Hz, 2H), 2.64 (s, 3H); MS (ES+) m/z 416.2 (M+1).

Sources & evidence

ORD record
ord-2a22c3bdf0d749a287416f89408ee57b
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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