1-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]methanamine → HCID 44552916, compound

HRID 714367Notes

Reaction equation

HRID 714367 reaction equation
O1C=C(CN)N=C1.[F:8][C:9]([F:18])([F:17])[C:10]1[S:11][CH:12]=[C:13]([CH2:15][NH2:16])[N:14]=1.[F:19][C:20]1[CH:41]=[CH:40][C:23]([CH2:24][N:25]2[CH2:29][CH2:28][N:27]([C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][N:38]=3)[C:33](O)=[O:34])[C:26]2=[O:39])=[CH:22][CH:21]=1>>[F:19][C:20]1[CH:21]=[CH:22][C:23]([CH2:24][N:25]2[CH2:29][CH2:28][N:27]([C:30]3[CH:31]=[C:32]([CH:36]=[CH:37][N:38]=3)[C:33]([NH:16][CH2:15][C:13]3[N:14]=[C:10]([C:9]([F:8])([F:17])[F:18])[S:11][CH:12]=3)=[O:34])[C:26]2=[O:39])=[CH:40][CH:41]=1

Participants

4

Reactant 3

HCID 177504151-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]methanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552916HCID 44552916, compoundYield 30%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (2-(trifluoromethyl)thiazol-4-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((2-(trifluoromethyl)thiazol-4-yl)methyl)isonicotinamide was obtained as a colorless solid in 30% yield: mp 66-68° C.; 1H NMR (300 MHz, CDCl3) δ 8.68 (s, 1H), 8.36 (d, J=5.1 Hz, 1H), 7.59 (s, 1H), 7.35 (d, J=5.1 Hz, 1H), 7.28-7.20 (m, 2H), 7.17-6.99 (m, 3H), 4.78 (d, J=6.0 Hz, 2H), 4.43 (s, 2H), 4.03 (t, J=8.0 Hz, 2H), 3.37 (t, J=8.0 Hz, 2H); MS (ES+) m/z 479.8 (M+1).

Sources & evidence

ORD record
ord-0cf6f68c99b34a8f9514fc260ddb65c6
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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