(4-methyl-2-phenyl-1,3-thiazol-5-yl)methanamine → HCID 44552917, compound

HRID 714368Notes

Reaction equation

HRID 714368 reaction equation
O1C=C(CN)N=C1.[CH3:8][C:9]1[N:10]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[S:12][C:13]=1[CH2:14][NH2:15].[F:22][C:23]1[CH:44]=[CH:43][C:26]([CH2:27][N:28]2[CH2:32][CH2:31][N:30]([C:33]3[CH:34]=[C:35]([CH:39]=[CH:40][N:41]=3)[C:36](O)=[O:37])[C:29]2=[O:42])=[CH:25][CH:24]=1>>[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][N:28]2[CH2:32][CH2:31][N:30]([C:33]3[CH:34]=[C:35]([CH:39]=[CH:40][N:41]=3)[C:36]([NH:15][CH2:14][C:13]3[S:12][C:11]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:10][C:9]=3[CH3:8])=[O:37])[C:29]2=[O:42])=[CH:43][CH:44]=1

Participants

4

Reactant 3

HCID 2795495(4-methyl-2-phenyl-1,3-thiazol-5-yl)methanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552917HCID 44552917, compoundYield 53%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (4-methyl-2-phenylthiazol-5-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((4-methyl-2-phenylthiazol-5-yl)methyl)isonicotinamide was obtained as a colorless solid in 53% yield: mp 182-184° C.; 1HNMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.36 (d, J=5.7 Hz, 1H), 7.87-7.84 (m, 2H), 7.42-7.37 (m, 4H), 7.24-7.20 (m, 2H), 7.03-6.93 (m, 3H), 4.75 (d, J=5.7 Hz, 2H), 4.40 (s, 2H), 4.02 (t, J=8.1 Hz, 2H), 3.35 (t, J=8.1 Hz, 2H), 2.49 (s, 3H); 13C NMR (75 MHz, CDCl3) δ 166.1, 165.6, 164.0, 160.7, 157.0, 153.0, 151.1, 148.5, 142.4, 133.6, 132.0, 129.9, 129.8, 128.9, 127.7, 126.4, 116.0, 115.8, 115.6, 109.0, 47.2, 41.3, 41.0, 35.8, 15.3; MS (ES+) m/z 501.9 (M+1).

Sources & evidence

ORD record
ord-f2091e82af9e45b3adbe384f8a27871b
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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