Trifluoroacetic acid → HCID 178510389, compound

HRID 2367790Notes

Reaction equation

HRID 2367790 reaction equation
[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:27][C:28]([C:30]2[N:31](COCC[Si](C)(C)C)[CH:32]=[C:33]([C:35]#[N:36])[N:34]=2)=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.[C:45]([OH:51])([C:47]([F:50])([F:49])[F:48])=[O:46]>C(Cl)Cl.CCO>[F:48][C:47]([F:50])([F:49])[C:45]([OH:51])=[O:46].[C:1]1([C:7]2[CH:12]=[C:11]([CH:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[CH:10]=[CH:9][C:8]=2[NH:27][C:28]([C:30]2[NH:31][CH:32]=[C:33]([C:35]#[N:36])[N:34]=2)=[O:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 56833954HCID 56833954, compound

Product 1

HCID 178510389HCID 178510389, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-cyano-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole-2-carboxylic acid {2-cyclohex-1-enyl-4-[1-(2-morpholin-4-yl-ethyl)-piperidin-4-yl]-phenyl}-amide (650 mg, 1.05 mmol) (as prepared in the previous step) in 10 mL of DCM was added 0.3 mL of EtOH and 3.0 mL of TFA, and the reaction was allowed to proceed for 2 h at 25° C. The reaction was diluted with 10 mL of EtOH and concentrated. The title compound was purified by RP-HPLC (C18), eluting with 30-50% CH3CN in 0.1% TFA/H2O over 9 min to give 600 mg (80%) of a white solid. 1H-NMR (400 MHz, CD3OD): δ 8.18 (d, 1H), 8.04 (s, 1H), 7.24 (dd, 1H), 7.14 (d, 1H), 5.84 (m, 1H), 3.84 (m, 4H), 3.76 (m, 2H), 3.50 (m, 2H), 3.30-3.10 (m, 4H), 2.92 (m, 5H), 2.30 (m, 4H), 2.20-2.00 (m, 4H), 1.90-1.74 (m, 4H). Mass spectrum (ESI, m/z): Calcd. for C28H36N6O2, 489.2. found 489.2.

Workup

  1. concentrationconcentrated
  2. customThe title compound was purified by RP-HPLC (C18)
  3. washeluting with 30-50% CH3CN in 0.1% TFA/H2O over 9 min

Sources & evidence

ORD record
ord-d205c3289a7d478ab0854346ba0f5f98
Source dataset
uspto-grants-2014_04
Patent number
US08697716B2

Reaction notes

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