1-(5-Methyl-1,2-oxazol-3-yl)methanamine → HCID 44552747, compound

HRID 714362Notes

Reaction equation

HRID 714362 reaction equation
O1C=C(CN)N=C1.[CH3:8][C:9]1[O:13][N:12]=[C:11]([CH2:14][NH2:15])[CH:10]=1.[F:16][C:17]1[CH:38]=[CH:37][C:20]([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[C:29]([CH:33]=[CH:34][N:35]=3)[C:30](O)=[O:31])[C:23]2=[O:36])=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:21][N:22]2[CH2:26][CH2:25][N:24]([C:27]3[CH:28]=[C:29]([CH:33]=[CH:34][N:35]=3)[C:30]([NH:15][CH2:14][C:11]3[CH:10]=[C:9]([CH3:8])[O:13][N:12]=3)=[O:31])[C:23]2=[O:36])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 27763061-(5-Methyl-1,2-oxazol-3-yl)methanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552747HCID 44552747, compoundYield 55%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (5-methylisoxazol-3-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((5-methylisoxazol-3-yl)methyl)isonicotinamide was obtained as a colorless solid in 55% yield: mp 153-155° C.; 1H NMR (300 MHz, CDCl3) δ 8.59 (s, 1H), 8.35 (d, J=5.1 Hz, 1H), 7.37-7.35 (m, 1H), 7.28-7.23 (m, 2H), 7.07-6.99 (m, 3H), 6.01 (s, 1H), 4.63 (d, J=5.7 Hz, 2H), 4.42 (s, 2H), 4.03 (t, J=8.1 Hz, 2H), 3.36 (t, J=8.1 Hz, 2H), 2.37 (s, 3H); MS (ES+) m/z 409.9 (M+1).

Sources & evidence

ORD record
ord-e23a9cbe1d934883918dd575f1e67ad5
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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