Oxazol-2-ylmethanamine → 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(oxazol-2-ylmethyl)isonicotinamide

HRID 714356Notes

Reaction equation

HRID 714356 reaction equation
O1C=C(CN)N=C1.[O: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[O: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 18947655Oxazol-2-ylmethanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 445553062-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(oxazol-2-ylmethyl)isonicotinamideYield 49%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with oxazol-2-ylmethanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(oxazol-2-ylmethyl)isonicotinamide was obtained as a colorless solid in 49% yield: mp 148-150° C.; 1H NMR (300 MHz, DMSO-d6) δ 9.36 (t, J=5.7 Hz, 1H), 8.60 (s, 1H), 8.38 (d, J=5.1 Hz, 2H), 8.03 (s, 1H), 7.36-7.31 (m, 3H), 7.18-7.07 (m, 2H), 4.55 (d, J=5.7 Hz, 2H), 4.39 (s, 2H), 3.94 (t, J=8.1 Hz, 2H), 3.45 (t, J=8.0 Hz, 2H); MS (ES+) m/z 396.0 (M+1).

Sources & evidence

ORD record
ord-c6c7db1ed15c478eb5a02b08f2a90971
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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