HCID 58994986, compound → HCID 178424445, compound

HRID 536948Notes

Reaction equation

HRID 536948 reaction equation
[CH3:1][C:2]1([CH3:43])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([C:20]4[N:21]=[N:22][NH:23][N:24]=4)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:25][C:26]([C:28]2[N:29](COCC[Si](C)(C)C)[CH:30]=[C:31]([C:33]#[N:34])[N:32]=2)=[O:27])=[CH:4][CH2:3]1>CO.C(Cl)Cl>[CH3:1][C:2]1([CH3:43])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]3([C:20]4[N:24]=[N:23][NH:22][N:21]=4)[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH:11]=[CH:10][C:9]=2[NH:25][C:26]([C:28]2[NH:29][CH:30]=[C:31]([C:33]#[N:34])[N:32]=2)=[O:27])=[CH:4][CH2:3]1

Participants

3

Reactant 1

HCID 58994986HCID 58994986, compound

Product 1

HCID 178424445HCID 178424445, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

The title compound was prepared by the procedure of Example 11, step (g) using 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid {2-(4,4-dimethyl-cyclohex-1-enyl)-4-[4-(2H-tetrazol-5-yl)-tetrahydro-pyran-4-yl]-phenyl}-amide (as prepared in the previous step, 51.2 mg, 0.0850 mmol). Silica gel chromatography (1-4% MeOH/DCM) afforded the title compound (17 mg, 43%) as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.26 (d, 1H, J=8.6 Hz), 7.90 (s, 1H), 7.22 (dd, 1H, J=8.6, 2.3 Hz), 7.12 (d, 1H, J=2.3 Hz), 5.73 (m, 1H), 3.95 (m, 2H), 3.54 (m, 2H), 2.70 (m, 2H), 2.42 (m, 2H), 2.26 (m, 2H), 2.08 (m, 2H), 1.58 (t, 2H, J=6.3 Hz), 1.09 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C25H28N8O2, 473.2 (M+H). found 473.2.

Workup

  1. customThe title compound was prepared by the procedure of Example 11, step (g)
  2. customas prepared in the previous step, 51.2 mg, 0.0850 mmol)

Sources & evidence

ORD record
ord-f842b6d4a4b24b9e91d9c84f5a52e454
Source dataset
uspto-grants-2014_10
Patent number
US08859602B2

Reaction notes

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