(1-methyl-1H-pyrazol-4-yl)methanamine → HCID 44552745, compound

HRID 714360Notes

Reaction equation

HRID 714360 reaction equation
O1C=C(CN)N=C1.[CH3:8][N:9]1[CH:13]=[C:12]([CH2:14][NH2:15])[CH:11]=[N: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:12]3[CH:11]=[N:10][N:9]([CH3:8])[CH:13]=3)=[O:31])[C:23]2=[O:36])=[CH:37][CH:38]=1

Participants

4

Reactant 3

HCID 671225(1-methyl-1H-pyrazol-4-yl)methanamineHCID 230556901,3-Oxazol-4-ylmethanamineHCID 582477912-(3-(4-Fluorobenzyl)-2-oxoimidazolidin-1-yl)isonicotinic acid

Product 1

HCID 44552745HCID 44552745, compoundYield 23%

Procedure

Following the procedure as described in Example 14, making variations as required to replace oxazol-4-ylmethanamine with (1-methyl-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-methyl-1H-pyrazol-4-yl)methyl)isonicotinamide was obtained as a colorless solid in 23% yield: mp 165-166° C.; 1HNMR (300 MHz, CDCl3) δ 8.52 (s, 1H), 8.34 (d, J=5.1 Hz, 1H), 7.44-7.37 (m, 3H), 7.27-7.22 (m, 2H), 7.04-6.98 (m, 2H), 6.70 (br s, 1H), 4.45-4.41 (m, 4H), 4.03 (t, J=8.1 Hz, 2H), 3.84 (s, 3H), 3.36 (t, J=8.1 Hz, 2H); 13C NMR (75 MHz, CDCl3) δ 165.5, 164.0, 160.7, 157.0, 152.9, 148.2, 143.0, 138.9, 132.1, 132.0, 129.9, 129.8, 116.0, 115.9, 115.6, 109.0, 47.2, 41.3, 41.0, 39.0, 34.5; MS (ES+) m/z 408.9 (M+1).

Sources & evidence

ORD record
ord-db000fce6942444283af8a52a177001c
Source dataset
uspto-grants-2015_11
Patent number
US09187426B2

Reaction notes

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