Ethanol → HCID 178486160, compound

HRID 1508077Notes

Reaction equation

HRID 1508077 reaction equation
[CH3:1][C:2]1([CH3:40])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][S:16](=[O:21])(=[O:20])[N:17]([CH3:19])[CH3:18])[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[N:26](COCC[Si](C)(C)C)[CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1.CCO.C(O)(C(F)(F)F)=O.CO>C(Cl)Cl>[CH3:1][C:2]1([CH3:40])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][S:16](=[O:21])(=[O:20])[N:17]([CH3:19])[CH3:18])[CH:11]=[CH:10][C:9]=2[NH:22][C:23]([C:25]2[NH:26][CH:27]=[C:28]([C:30]#[N:31])[N:29]=2)=[O:24])=[CH:4][CH2:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 887MethanolHCID 6422Trifluoroacetic acidHCID 58994426HCID 58994426, compound

Product 1

HCID 178486160HCID 178486160, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 355 mg (0.606 mmol) of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-(4,4-dimethyl-cyclohex-1-enyl)-4-(2-dimethylsulfamoyl-ethyl)-phenyl]-amide (as prepared in the previous step) in CH2Cl2 (15 mL) was treated with EtOH (300 μL) and TFA (1.5 mL) at RT for 24 h. MeOH (20 mL) was added, and the solvents were evaporated in vacuo. The solid was triturated with acetonitrile to afford 169 mg (61%) of the title compound as a white solid: 1H-NMR (CD3CN; 400 MHz): δ 9.41 (s, 1H), 8.23 (d, 1H, J=8.0 Hz), 7.91 (s, 1H), 7.22 (d, 1H, J=8.0 Hz), 7.18 (s, 1H), 5.80-5.71 (m, 1H), 3.31-3.21 (m, 2H), 3.10-3.00 (m, 2H), 2.85 (s, 6H), 2.37-2.27 (m, 2H), 2.10-2.04 (m, 2H), 1.64-1.55 (m, 2H), 1.10 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C23H29N5O3S, 456.2 (M+H). found 456.1.

Workup

  1. customthe solvents were evaporated in vacuo
  2. customThe solid was triturated with acetonitrile

Sources & evidence

ORD record
ord-6aba206b40044bb2b5025dafa26a7d74
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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