1,3-Oxazol-4-ylmethanamine → HCID 178523064, compound

HRID 714361Notes

Reaction equation

HRID 714361 reaction equation
O1C=C(CN)N=C1.[NH: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>>[NH:8]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:29](=[O:30])[C:28]2[CH:32]=[CH:33][N:34]=[C:26]([N:23]3[CH2:24][CH2:25][N:21]([CH2:20][C:19]4[CH:18]=[CH:17][C:16]([F:15])=[CH:37][CH:36]=4)[C:22]3=[O:35])[CH:27]=2)=[N:9]1

Participants

4

Reactant 3

HCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acidHCID 178510230HCID 178510230, compound

Product 1

HCID 178523064HCID 178523064, compoundYield 23%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (1H-pyrazol-3-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, N-((1H-pyrazol-3-yl)methyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 23% yield: mp 178-180° C.; 1H NMR (300 MHz, CDCl3) δ 8.60 (s, 1H), 8.33-8.24 (m, 2H), 7.45-7.37 (m, 2H), 7.32-7.17 (m, 3H), 7.04-6.94 (m, 2H), 6.27 (s, 1H), 4.70 (d, J=5.7 Hz, 2H), 4.43 (s, 2H), 4.03 (t, J=8.1 Hz, 2H), 3.37 (t, J=8.1 Hz, 2H); MS (ES+) m/z 394.9 (M+1).

Sources & evidence

ORD record
ord-d158313b20a54ee8b64036fc6b813482
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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