Isoxazol-3-ylmethanamine → HCID 44552915, compound

HRID 714366Notes

Reaction equation

HRID 714366 reaction equation
O1C=C(CN)N=C1.[O:8]1[CH:12]=[CH:11][C:10]([CH2:13][NH2:14])=[N:9]1.[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:10]3[CH:11]=[CH:12][O:8][N:9]=3)=[O:30])[C:22]2=[O:35])=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 15079262Isoxazol-3-ylmethanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552915HCID 44552915, compoundYield 53%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with isoxazol-3-ylmethanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-(isoxazol-3-ylmethyl)isonicotinamide was obtained as a colorless solid in 53% yield: mp 127-129° C.; 1H NMR (300 MHz, CDCl3) δ 8.61 (s, 1H), 8.37-8.34 (m, 2H), 7.36 (dd, J=5.1 Hz, 1.2 Hz, 1H), 7.31-7.23 (m, 2H), 7.04-6.98 (m, 3H), 6.39 (d, J=1.5 Hz, 1H), 4.73 (d, J=6.0 Hz, 2H), 4.42 (s, 2H), 4.03 (t, J=8.1 Hz, 2H), 3.36 (t, J=8.1 Hz, 2H); MS (ES+) m/z 395.7 (M+1).

Sources & evidence

ORD record
ord-add1be56c97a4459b77af3477d7ee167
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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