Trifluoroacetic acid → HCID 11546582, compound

HRID 646864Notes

Reaction equation

HRID 646864 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[C:12]([N: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[O:24][C:25]([C:28]#[N:29])=[CH:26][CH:27]=2)=[O:22])[CH2:4][CH2:3]1.F[C:31](F)(F)[C:32](O)=[O:33].C(OC(=O)C)(=O)C.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>C1COCC1>[C:32]([N:17]1[CH2:18][CH2:19][N:14]([C:12]2[CH:11]=[CH:10][C:9]([NH:20][C:21]([C:23]3[O:24][C:25]([C:28]#[N:29])=[CH:26][CH:27]=3)=[O:22])=[C:8]([N:5]3[CH2:4][CH2:3][CH:2]([CH3:1])[CH2:7][CH2:6]3)[CH:13]=2)[CH2:15][CH2:16]1)(=[O:33])[CH3:31]

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 11714690HCID 11714690, compound

Product 1

HCID 11546582HCID 11546582, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 40.0 mg (0.0546 mmol) of 5-cyano-furan-2-carboxylic acid [2-(4-methyl-piperidin-1-yl)-4-piperazin-1-yl-phenyl]-amide tris(trifluoroacetic acid salt) (as prepared in Example 16) suspended in 2 mL of anh THF was added 6.2 μL (0.0655 mmol) of acetic anhydride followed by 47.6 μL (0.716 mmol) of DIEA. After stirring for 20 min at RT, the mixture was poured into satd aq NaHCO3 (20 mL) and extracted with EtOAc (20 mL). The extract was dried (Na2SO4) and concentrated in vacuo and the resulting solid was chromatographed on a 2-g silica SPE column with 25-40% EtOAc-dichloromethane to afford 22.0 mg (92%) of the title compound as a crystalline yellow solid: 1H-NMR (CDCl3; 400 MHz): δ 9.59 (br s, 1H), 8.32 (d, 1H, J=8.9 Hz), 7.22, 7.25 (AB q, 2H, J=3.7 Hz, partially obscured by CHCl3 peak), 6.79 (d, 1H, J=2.6 Hz), 6.72 (dd, 1H, J=8.9, 2.6 Hz), 3.77-3.80 (m, 2H), 3.62-3.64 (m, 2H), 3.11-3.17 (m, 4H), 2.98-3.01 (m, 2H), 2.73-2.76 (m, 2H), 2.15 (s, 3H), 1.83-1.86 (m, 2H), 1.52-1.62 (m, 1H), 1.46-1.56 (m, 2H) and 1.07 (d, 3H, J=6.2 Hz). Mass spectrum (ESI, m/z): Calcd. for C24H29N5O3, 436.2 (M+H), found 436.2.

Workup

  1. extractionextracted with EtOAc (20 mL)
  2. dry with materialThe extract was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customthe resulting solid was chromatographed on a 2-g silica SPE column with 25-40% EtOAc-dichloromethane

Sources & evidence

ORD record
ord-b5df8752e0e14f37ac21e5e31c245518
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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