1-(1,5-Dimethyl-1H-pyrazol-3-yl)methanamine → HCID 44552748, compound

HRID 714363Notes

Reaction equation

HRID 714363 reaction equation
O1C=C(CN)N=C1.[CH3:8][N:9]1[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][NH2:16])=[N:10]1.[F:17][C:18]1[CH:39]=[CH:38][C:21]([CH2:22][N:23]2[CH2:27][CH2:26][N:25]([C:28]3[CH:29]=[C:30]([CH:34]=[CH:35][N:36]=3)[C:31](O)=[O:32])[C:24]2=[O:37])=[CH:20][CH:19]=1>>[CH3:8][N:9]1[C:13]([CH3:14])=[CH:12][C:11]([CH2:15][NH:16][C:31](=[O:32])[C:30]2[CH:34]=[CH:35][N:36]=[C:28]([N:25]3[CH2:26][CH2:27][N:23]([CH2:22][C:21]4[CH:20]=[CH:19][C:18]([F:17])=[CH:39][CH:38]=4)[C:24]3=[O:37])[CH:29]=2)=[N:10]1

Participants

4

Reactant 3

HCID 27763671-(1,5-Dimethyl-1H-pyrazol-3-yl)methanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552748HCID 44552748, compoundYield 70%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (1,5-dimethyl-1H-pyrazol-3-yl)methanamine to react with 2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid, N-((1,5-dimethyl-1H-pyrazol-3-yl)methyl)-2-(3-(4-fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinamide was obtained as a colorless solid in 70% yield: mp 150-152° C.; 1H NMR (300 MHz, CDCl3) δ 8.57 (s, 1H), 8.33 (d, J=5.1 Hz, 1H), 7.38-7.36 (m, 1H), 7.28-7.23 (m, 2H), 7.05-6.97 (m, 2H), 6.87 (br s, 1H), 5.98 (s, 1H), 4.53 (d, J=5.1 Hz, 2H), 4.42 (s, 2H), 4.02 (t, J=8.1 Hz, 2H), 3.71 (s, 3H), 3.35 (t, J=8.1 Hz, 2H), 2.21 (s, 3H); MS (ES+) m/z 422.9 (M+1).

Sources & evidence

ORD record
ord-713d6c0d4b1340d39769e5f348d43fc5
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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