Trifluoroacetic acid → HCID 178510435, compound

HRID 1008902Notes

Reaction equation

HRID 1008902 reaction equation
[C:1](O)(C(F)(F)F)=[O:2].[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:25][NH:24][S:23](=[O:27])(=[O:26])[NH:22][CH2:21]3)[CH:17]=[CH:16][C:15]=2[NH:28][C:29]([C:31]2[N:32](COCC[Si](C)(C)C)[CH:33]=[C:34]([C:36]#[N:37])[N:35]=2)=[O:30])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1>C(Cl)Cl.CCO>[C:8]1([C:14]2[CH:19]=[C:18]([CH:20]3[CH2:25][NH:24][S:23](=[O:26])(=[O:27])[NH:22][CH2:21]3)[C:17]([CH2:1][OH:2])=[CH:16][C:15]=2[NH:28][C:29]([C:31]2[NH:32][CH:33]=[C:34]([C:36]#[N:37])[N:35]=2)=[O:30])[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 597711354-Cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1,1-dioxo-1lambda6-[1,2,6]thiadiazinan-4-yl)-phenyl]-amide

Product 1

HCID 178510435HCID 178510435, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

TFA (0.3 mL) was added to a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid [2-cyclohex-1-enyl-4-(1,1-dioxo-1λ6-[1,2,6]thiadiazinan-4-yl)-phenyl]-amide (as prepared in Example 5, step (d), 21 mg, 0.030 mmol) in DCM (1 mL) and EtOH (30 μL). The resulting mixture was stirred at RT for 2 h and concentrated in vacuo. The residue obtained was purified on silica (20-50% EtOAc-hexane) to obtain the title compound (8.0 mg, 46%): 1H-NMR (CD3OD; 400 MHz): δ 8.10 (s, 1H), 8.05 (s, 1H), 7.11 (s, 1H), 5.78 (br s, 1H), 4.7 (ABq, 1H, J=16 Hz), 4.48 (ABq, 1H, J=16 Hz), 4.3 (m, 1H), 3.87 (m, 1H), 3.52 (m, 1H), 3.6 (m, 1H), 3.18 (m, 1H), 2.62 (br s, 1H), 2.22-2.34 (m, 4H), 1.72-1.90 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C21H24N6O4S, 439.1 (M−H2O+H). found 439.2.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue obtained
  3. customwas purified on silica (20-50% EtOAc-hexane)

Sources & evidence

ORD record
ord-1db16c6485064ac0a5fb05ad238d5d46
Source dataset
uspto-grants-2011_07
Patent number
US07973035B2

Reaction notes

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