Acetic Acid → HCID 23502756, compound

HRID 1835111Notes

Reaction equation

HRID 1835111 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[CH2:9][CH2:10][CH2:11][NH:12][CH:13]([C:21]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:28])[CH2:14][N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.CCN(C(C)C)C(C)C.[C:38](O)(=[O:40])[CH3:39].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C>[F:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH2:9][CH2:10][CH2:11][N:12]([CH:13]([C:21]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=1[CH3:28])[CH2:14][N:15]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1)[C:38](=[O:40])[CH3:39]

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 23502703HCID 23502703, compound

Product 1

HCID 23502756HCID 23502756, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

150 mg (0.39 mmol) of [3-(2,6-difluorophenyl)propyl]-[1-(2,6-dimethylphenyl)-2-piperidin-1-ylethyl]amine (corresponds to Example 35) is placed in 3 ml of THF. Then 0.07 ml of DIPEA and 0.02 ml (0.39 mmol) of acetic acid are added; and finally 124.6 mg (0.39 mmol) of TBTU are added. The mixture is then stirred for 6 hours at room temperature, the solvent is eliminated, ethyl acetate and saturated NaHCO3 solution are added, and the resulting mixture is stirred for 15 minutes. The phases are separated and the organic phase is washed twice more with NaHCO3 solution and twice with saturated NaCl solution. The organic phase is dried and evaporated down and the residue is purified by flash chromatography (cyclohexane/ethyl acetate 7:3). MS: m/z 429 [(M+H)+].

Workup

  1. stirringthe resulting mixture is stirred for 15 minutes
  2. customThe phases are separated
  3. washthe organic phase is washed twice more with NaHCO3 solution and twice with saturated NaCl solution
  4. customThe organic phase is dried
  5. customevaporated down
  6. customthe residue is purified by flash chromatography (cyclohexane/ethyl acetate 7:3)

Sources & evidence

ORD record
ord-6f7543cc8a2d4e6ba87453881a3a508d
Source dataset
uspto-grants-2004_08
Patent number
US06770636B2

Reaction notes

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