1,3-Thiazol-2-ylmethanamine → HCID 44555305, compound

HRID 714355Notes

Reaction equation

HRID 714355 reaction equation
O1C=C(CN)N=C1.[S:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][NH2:14].[F:15][C:16]1[CH:37]=[CH:36][C:19]([CH2:20][N:21]2[CH2:25][CH2:24][N:23]([C:26]3[CH:27]=[C:28]([CH:32]=[CH:33][N:34]=3)[C:29](O)=[O:30])[C:22]2=[O:35])=[CH:18][CH:17]=1>>[F:15][C:16]1[CH:17]=[CH:18][C:19]([CH2:20][N:21]2[CH2:25][CH2:24][N:23]([C:26]3[CH:27]=[C:28]([CH:32]=[CH:33][N:34]=3)[C:29]([NH:14][CH2:13][C:9]3[S:8][CH:12]=[CH:11][N:10]=3)=[O:30])[C:22]2=[O:35])=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 27565071,3-Thiazol-2-ylmethanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44555305HCID 44555305, compoundYield 88%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with thiazol-2-ylmethanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(thiazol-2-ylmethyl)isonicotinamide was obtained as a colorless solid in 88% yield: mp 123-125° C.; NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 8.35 (d, J=5.1 Hz, 1H), 7.70 (d, J=2.7 Hz, 1H), 7.39-7.21 (m, 5H), 7.04-6.99 (m, 2H), 4.93 (d, J=5.7 Hz, 2H), 4.42 (s, 2H), 4.02 (t, J=8.1 Hz, 2H), 3.36 (t, J=8.1 Hz, 2H); MS (ES+) m/z 411.9 (M+1).

Sources & evidence

ORD record
ord-ea92b51f31324b2d81f184b24fa45257
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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