Potassium → HCID 86609180, compound

HRID 1711329Notes

Reaction equation

HRID 1711329 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:7][CH2:6][N:5]([C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:4][CH2:3]1.[C:16]([C:18]1[N:19]=[C:20]([C:31](O)=[O:32])[N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=1)#[N:17].[K]>>[CH3:1][C:2]1([CH3:15])[CH2:3][CH2:4][N:5]([C:8]2[C:13]([NH:14][C:31]([C:20]3[N:21]([CH2:23][O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH:22]=[C:18]([C:16]#[N:17])[N:19]=3)=[O:32])=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 5462222PotassiumHCID 591285854-Cyano-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole-2-carboxylic acidHCID 62937925HCID 62937925, compound

Product 1

HCID 86609180HCID 86609180, compound

Procedure

4,4-Dimethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-ylamine (as prepared in above step) was coupled with 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid, potassium salt (as prepared in Example 11, step (d), as described in Example 32, step (c) to afford 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid (4,4-dimethyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl)-amide which was subjected to SEM deprotection as described in Example 47, step (d) to afford the title compound. 1H-NMR (DMSO-d6; 400 MHz): δ 14.4 (s, 1H), 9.72 (s, 1H), 8.39 (m, 2H), 8.11 (dd, 1H, J=4.8, 1.7 Hz), 7.13 (dd, 1H, J=4.8, 1.7 Hz), 3.02 (m, 4H), 1.56 (m, 4H), 1.01 (s, 6H); Mass spectrum (ESI, m/z): Calcd. for C17H20N6O, 325.1 (M+H), found 325.2.

Workup

  1. customas prepared in Example 11, step (d)

Sources & evidence

ORD record
ord-007859602403492180af17b91c6c50d1
Source dataset
uspto-grants-2010_09
Patent number
US07790724B2

Reaction notes

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