(1,3,5-trimethyl-1H-pyrazol-4-yl)methylamine → HCID 44552744, compound

HRID 714359Notes

Reaction equation

HRID 714359 reaction equation
O1C=C(CN)N=C1.[CH3:8][N:9]1[C:13]([CH3:14])=[C:12]([CH2:15][NH2:16])[C:11]([CH3:17])=[N:10]1.[F:18][C:19]1[CH:40]=[CH:39][C:22]([CH2:23][N:24]2[CH2:28][CH2:27][N:26]([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=3)[C:32](O)=[O:33])[C:25]2=[O:38])=[CH:21][CH:20]=1>>[F:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:23][N:24]2[CH2:28][CH2:27][N:26]([C:29]3[CH:30]=[C:31]([CH:35]=[CH:36][N:37]=3)[C:32]([NH:16][CH2:15][C:12]3[C:11]([CH3:17])=[N:10][N:9]([CH3:8])[C:13]=3[CH3:14])=[O:33])[C:25]2=[O:38])=[CH:39][CH:40]=1

Participants

4

Reactant 3

HCID 2776430(1,3,5-trimethyl-1H-pyrazol-4-yl)methylamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552744HCID 44552744, compoundYield 67%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (1,3,5-trimethyl-1H-pyrazol-4-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)-N-((1,3,5-trimethyl-1H-pyrazol-4-yl)methyl)isonicotinamide was obtained as a colorless solid in 67% yield: mp 179-181° C.; 1H NMR (300 MHz, CDCl3) δ 8.48 (s, 1H), 8.33 (d, J=5.1 Hz, 1H), 7.37 (dd, J=5.1 Hz, 1.2 Hz, 1H), 7.25-7.21 (m, 2H), 7.03-6.97 (m, 2H), 6.35 (br s, 1H), 4.40-4.36 (m, 4H), 4.01 (t, J=8.1 Hz, 2H), 3.68 (s, 3H), 3.34 (t, J=8.1 Hz, 2H), 2.21 (s, 3H), 2.19 (s, 3H); MS (ES+) m/z 436.8 (M+1).

Sources & evidence

ORD record
ord-962af54bb1204edf86e7973ec5361b6a
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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