Trifluoroacetic acid → HCID 178424530, compound

HRID 1508068Notes

Reaction equation

HRID 1508068 reaction equation
[CH3:1][C:2]1([CH3:43])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][S:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)(=[O:18])=[O:17])[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.C(O)(C(F)(F)F)=O>C(Cl)Cl.CCO>[CH3:1][C:2]1([CH3:43])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([CH2:14][CH2:15][S:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)(=[O:17])=[O:18])[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

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 589944894-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid {2-(4,4-dimethyl-cyclohex-1-enyl)-4-[2-(morpholine-4-sulfonyl)-ethyl]-pheny}-amide

Product 1

HCID 178424530HCID 178424530, compound

Reagents, catalysts & solvents 2

HCID 702EthanolCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 60.3 mg of crude 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid {2-(4,4-dimethyl-cyclohex-1-enyl)-4-[2-(morpholine-4-sulfonyl)-ethyl]-phenyl}-amide (as prepared in the previous step) in CH2Cl2 (5 mL) was treated with EtOH (2 drops) and TFA (1 mL) and stirred at RT for 1.5 h. Solvents were evaporated in vacuo, and the residue was purified by RP-HPLC(C18) with 20-100% CH3CN in 0.1% TFA/H2O over 30 min to afford 11.2 mg (20% over three steps) of the title compound as a white solid: 1H-NMR (CD3OD; 400 MHz): δ 8.16 (d, 1H, J=8.4 Hz), 7.91 (s, 1H), 7.21 (dd, 1H, J=8.4, 2.4 Hz), 5.76-5.71 (m, 1H), 3.71-3.65 (m, 4H), 3.50-3.46 (m, 1H), 3.26-3.20 (m, 4H), 3.14-3.11 (m, 1H), 3.10-3.04 (m, 2H), 3.35-2.27 (m, 2H), 2.10-2.05 (m, 2H), 1.59 (t, 2H, J=6.4 Hz), 1.08 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C25H31N5O4S, 498.2 (M+H). found 498.0.

Workup

  1. customSolvents were evaporated in vacuo
  2. customthe residue was purified by RP-HPLC(C18) with 20-100% CH3CN in 0.1% TFA/H2O over 30 min

Sources & evidence

ORD record
ord-b95e586c339e4192af2ff3753c44db1c
Source dataset
uspto-grants-2015_12
Patent number
US09221797B2

Reaction notes

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