4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenyl]-amide → HCID 178428186, compound

HRID 646914Notes

Reaction equation

HRID 646914 reaction equation
[O:1]=[S:2]1(=[O:39])[CH2:7][CH2:6][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[N:18](COCC[Si](C)(C)C)[CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[C:10]([N:32]3[CH2:37][CH2:36][CH:35]([CH3:38])[CH2:34][CH2:33]3)[CH:9]=2)[CH2:4][CH2:3]1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[O:39]=[S:2]1(=[O:1])[CH2:3][CH2:4][CH:5]([C:8]2[CH:13]=[CH:12][C:11]([NH:14][C:15]([C:17]3[NH:18][CH:19]=[C:20]([C:22]#[N:23])[N:21]=3)=[O:16])=[C:10]([N:32]3[CH2:37][CH2:36][CH:35]([CH3:38])[CH2:34][CH2:33]3)[CH:9]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 1

HCID 586385334-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(1,1-dioxo-hexahydro-1lambda6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenyl]-amide

Product 1

HCID 178428186HCID 178428186, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [4-(1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-2-(4-methyl-piperidin-1-yl)-phenyl]-amide (as prepared in the previous step, 19.0 mg, 0.0330 mmol) in 1 mL of 2:1 TFA/DCM was stirred at RT for 4 h. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (10-20% EtOAc/DCM) gave 13.2 mg (90%) of the title compound as a white solid: 1H-NMR (CDCl3; 400 MHz): δ 12.00 (s, 1H), 10.29 (s, 1H), 8.33 (d, 1H, J=8.3 Hz), 7.76 (d, 1H, J=2.3 Hz), 7.12 (dd, 1H, J=8.3, 1.7 Hz), 7.06 (d, 1H, J=1.7 Hz), 3.14-3.22 (m, 4H), 3.01 (d, 2H, J=12.0 Hz), 2.68-2.83 (m, 3H), 2.38-2.53 (m, 2H), 2.23 (d, 2H, J=14.5 Hz), 1.50-1.85 (m, 5H), 1.09 (d, 3H, J=5.8 Hz). Mass spectrum (ESI, m/z): Calcd. for C22H27N5O3S, 442.2 (M+H), found 442.2.

Workup

  1. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-0bc2bbe3c70644309644c3d9b8fb3d7d
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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