(4-methyl-4H-1,2,4-triazol-3-yl)methanamine → 5-Butyl-1-(5-methyl-4-(thiazol-5-yl)pyrimidin-2-yl)-N-((4-methyl-4H-1,2,4-triazol-3-yl)methyl)-1H-pyrazole-4-carboxamide

HRID 910258Notes

Reaction equation

HRID 910258 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:20][CH:19]=[N:18][CH:17]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[C:22](O)=[O:23])[CH2:2][CH2:3][CH3:4].S1C(B(O)O)=CN=C1.[CH3:33][N:34]1[CH:38]=[N:37][N:36]=[C:35]1[CH2:39][NH2:40]>>[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:20][CH:19]=[N:18][CH:17]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[C:22]([NH:40][CH2:39][C:35]1[N:34]([CH3:33])[CH:38]=[N:37][N:36]=1)=[O:23])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 21744036(4-methyl-4H-1,2,4-triazol-3-yl)methanamineHCID 45121658Thiazol-5-ylboronic acidHCID 60207815HCID 60207815, compound

Product 1

HCID 248989545-Butyl-1-(5-methyl-4-(thiazol-5-yl)pyrimidin-2-yl)-N-((4-methyl-4H-1,2,4-triazol-3-yl)methyl)-1H-pyrazole-4-carboxamide

Procedure

Compound 27 was prepared from 5-butyl-1-(5-methyl-4-(thiazol-5-yl)pyrimidin-2-yl)-1H-pyrazole-4-carboxylic acid following procedures described in Example 1 with the exceptions of substituting thiophene-2-boronic acid with thiazole-5-boronic acid in Step 1 and substituting pyridine-4-ylmethylamine with (4-methyl-4H-1,2,4-triazol-3-yl)methanamine. 1H NMR (400 MHz, MeOD-d3) δ 0.85 (t, J=7.3 Hz, 3H), 1.36 (m, 2H), 1.61 (m, 2H), 2.69 (s, 3H), 3.56 (t, J=7.4 Hz, 2H), 3.97 (s, 3H), 4.81 (s, 2H), 7.63 (s, 1H), 8.15 (s, 1H), 8.61 (s, 1H), 8.81 (s, 1H), 8.98 (s, 1H), 9.17 (s, 1H). LCMS (ES+) m/z 438 (M+1).

Sources & evidence

ORD record
ord-541f64d372674d11847b541497cde905
Source dataset
uspto-grants-2011_09
Patent number
US08022061B2

Reaction notes

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