Diisopropylethylamine → N-((5-Butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methyl)-1,2-dimethyl-1H-imidazole-5-sulfonamide

HRID 910263Notes

Reaction equation

HRID 910263 reaction equation
[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[CH2:22][NH2:23])[CH2:2][CH2:3][CH3:4].[CH3:24][N:25]1[C:29]([S:30](Cl)(=[O:32])=[O:31])=[CH:28][N:27]=[C:26]1[CH3:34].C(N(C(C)C)CC)(C)C>ClCCl>[CH2:1]([C:5]1[N:9]([C:10]2[N:15]=[C:14]([C:16]3[S:17][CH:18]=[CH:19][CH:20]=3)[C:13]([CH3:21])=[CH:12][N:11]=2)[N:8]=[CH:7][C:6]=1[CH2:22][NH:23][S:30]([C:29]1[N:25]([CH3:24])[C:26]([CH3:34])=[N:27][CH:28]=1)(=[O:32])=[O:31])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27362581,2-dimethyl-1H-imidazole-5-sulfonyl chlorideHCID 60207818(5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methanamine

Product 1

HCID 60207824N-((5-Butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methyl)-1,2-dimethyl-1H-imidazole-5-sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by mixing a sample of (5-butyl-1-(5-methyl-4-(thiophen-2-yl)pyrimidin-2-yl)-1H-pyrazol-4-yl)methanamine, (from Step 3 of Example 36), 1,2-dimethyl-1H-imidazole-5-sulfonyl chloride and diisopropylethylamine in dichloromethane. 1H NMR (400 MHz, CD3OD) δ 8.68 (s 1H), 7.94 (m, 1H), 7.78 (m, 1H), 7.56 (m, 1H), 7.37 (m, 1H), 7.29 (m, 1H), 4.09 (s 2H), 3.70 (s 3H), 3.18 (br t, 2H), 2.64 (s, 3H), 2.35 (s, 3H), 1.49 (m, 2H), 1.32 (m, 2H), 0.84 (m 3H). LCMS (ES+) m/z 486 (M+1).

Sources & evidence

ORD record
ord-6fa50c23e1c243999b8647c07ca75cd8
Source dataset
uspto-grants-2011_09
Patent number
US08022061B2

Reaction notes

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