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Propionic Acid → HCID 178460241, compound

HRID 2042413
Notes
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Reaction equation

HRID 2042413 reaction equation
Cl.Cl.Cl.[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH2:27])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH:6]=[CH:5]1.[C:28](O)(=[O:31])[CH2:29][CH3:30].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C([O-])(O)=O.[Na+]>CN(C=O)C>[O:4]1[C:12]2[CH:11]=[CH:10][N:9]=[C:8]([N:13]3[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][C@H:21]4[CH2:26][CH2:25][C@H:24]([NH:27][C:28](=[O:31])[CH2:29][CH3:30])[CH2:23][CH2:22]4)[CH2:15][CH2:14]3)[C:7]=2[CH:6]=[CH:5]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 1032Propionic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178478592HCID 178478592, compound2×

Product 1

HCID 178460241
HCID 178460241, compound
Yield 94.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution in DMF (1.5 ml) of trans-4-[2-(4-furo[3,2-c]pyridin-4-yl-piperazin-1-yl)-ethyl]-cyclohexylamine trihydrochloride (intermediate A) (150 mg, 0.34 mmol) were added propionic acid (27 mg, 0.36 mmol), DIPEA (177 mg, 1.37 mmol) and TBTU (115 mg, 0.36 mmol). The reaction mixture was stirred over night at room temperature then sat. aq. NaHCO3 sol. was added and the product was extracted with EtOAc. After drying (Na2SO4) the solvent was evaporated and the product was purified by flash chromatography on silica gel (CH2Cl2/MeOH/25% NH3 aq 140:10:1) to yield the title compound as a white solid (123 mg, 93%), MS (ISP) m/z=385.3 [(M+H)+].

Workup

  1. extractionthe product was extracted with EtOAc
  2. dry with materialAfter drying (Na2SO4) the solvent
  3. customwas evaporated
  4. customthe product was purified by flash chromatography on silica gel (CH2Cl2/MeOH/25% NH3 aq 140:10:1)

Sources & evidence

ORD record
ord-5e207bd87da64fc986b7f0fc52e15835
Source dataset
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08586579B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes