Trifluoroacetic acid → HCID 11533182, compound

HRID 646906Notes

Reaction equation

HRID 646906 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][C:9]=2[NH:20][C:21]([C:23]2[NH:24][CH:25]=[C:26]([C:28]#[N:29])[CH:27]=2)=[O:22])[CH2:4][CH2:3]1.FC(F)(F)C(O)=O.C([O-])([O-])=O.[Na+].[Na+].[C:43](N1C=CN=C1)([N:45]1[CH:49]=[CH:48][N:47]=[CH:46]1)=[O:44]>CN(C=O)C.C1COCC1.CCOC(C)=O>[N:45]1([C:43]([N:17]2[CH2:18][CH2:19][CH:14]([C:12]3[CH:11]=[CH:10][C:9]([NH:20][C:21]([C:23]4[NH:24][CH:25]=[C:26]([C:28]#[N:29])[CH:27]=4)=[O:22])=[C:8]([N:5]4[CH2:6][CH2:7][CH:2]([CH3:1])[CH2:3][CH2:4]4)[CH:13]=3)[CH2:15][CH2:16]2)=[O:44])[CH:49]=[CH:48][N:47]=[CH:46]1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 11671730HCID 11671730, compound

Product 1

HCID 11533182HCID 11533182, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-cyano-1H-pyrrole-2-carboxylic acid [2-(4-methyl-piperidin-1-yl)-4-piperidin-4-yl-phenyl]-amide bis(trifluoroacetic acid salt) (as prepared in Example 35, 20.0 mg, 0.0320 mmol) and anh Na2CO3 (6.8 mg, 0.065 mmol) in 0.30 mL of DMF was added carbonyldiimidazole (11 mg, 0.068 mmol) in 0.3 mL of THF at RT. The mixture was stirred at RT for 2 h. Treated with 20 mL of EtOAc, the mixture was washed with H2O, brine and dried with Na2SO4. Removal of the solvent under reduced pressure followed by flash chromatography of the residue on silica gel (1-5% MeOH/DCM) gave 14 mg (86%) of the title compound as a white solid: 1H-NMR (CDCl3; 400 MHz): δ 10.7 (s, 1H), 9.16 (s, 1H), 8.33 (d, 1H, J=8.3 Hz), 7.95 (s, 1H), 7.47 (s, 1H), 7.13 (s, 1H), 7.06 (s, 1H), 7.03 (s, 1H), 6.88 (s, 1H), 4.28 (d, 2H, J=12.9 Hz), 3.16 (d, 2H, J=12.0 Hz), 2.97 (d, 2H, J=11.6 Hz), 2.71-2.84 (m, 3H), 1.99 (d, 2H, J=12.1 Hz), 1.87 (d, 2H, J=12.1 Hz), 1.71-1.83 (m, 2H), 1.65 (s, 1H), 1.54-1.65 (m, 1H), 1.34-1.48 (m, 2H), 1.10 (d, 3H, J=6.5 Hz). Mass spectrum (ESI, m/z): Calcd. for C27H31N7O2, 486.2 (M+H), found 486.0.

Workup

  1. washthe mixture was washed with H2O, brine
  2. dry with materialdried with Na2SO4
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-6fead8d959bf4059a4a423b98bcba9bc
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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