Trifluoroacetic acid → HCID 11634981, compound

HRID 1992007Notes

Reaction equation

HRID 1992007 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[N:25](COCC[Si](C)(C)C)[CH:26]=[C:27]([C:29]#[N:30])[N:28]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:39]([OH:45])([C:41]([F:44])([F:43])[F:42])=[O:40]>C(Cl)Cl.CCO>[F:42][C:41]([F:44])([F:43])[C:39]([OH:45])=[O:40].[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([O:19][CH3:20])[CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:21][C:22]([C:24]2[NH:28][C:27]([C:29]#[N:30])=[CH:26][N:25]=2)=[O:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 59128589HCID 59128589, compound

Product 1

HCID 11634981HCID 11634981, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1-methoxy-piperidin-4-yl)-phenyl]-amide (as prepared in previous step, 31 mg, 0.020 mmol) in DCM (0.5 mL) and EtOH (11 μL) was added TFA (0.1 mL). The resulting solution was stirred at RT for 6 h. The reaction mixture was concentrated in vacuo and the resulting residue was dried for 1 h, suspended in ether (10 mL) and sonicated for 5 min. The solid formed was collected by suction filtration to obtain the title compound (17.3 mg, 58%). 1H-NMR (DMSO; 400 MHz): δ 9.70 (s, 1H), 8.30 (s, 1H), 7.83 (d, 1H, J=8.4 Hz), 7.14 (d, 1H, J=8.4 Hz), 7.05 (s, 1H), 5.71 (br s, 1H), 3.30-3.55 (m, 5H), 2.41-2.62 (m, 2H), 2.12-2.19 (m, 4H), 1.60-1.85 (m, 8H). Mass spectrum (ESI, m/z): Calcd. for C23H27N5O2, 406.2 (M+H), found 406.1.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe resulting residue was dried for 1 h
  3. customsonicated for 5 min
  4. customThe solid formed
  5. filtrationwas collected by suction filtration

Sources & evidence

ORD record
ord-e1e88730159e4f33bb8ed96411f07d43
Source dataset
uspto-grants-2010_01
Patent number
US07645755B2

Reaction notes

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