Triethylamine → HCID 66750896, compound

HRID 534951Notes

Reaction equation

HRID 534951 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH:2]1[C:6]([OH:8])=O.Cl.[CH3:10][N:11]([CH3:20])[CH2:12][CH2:13][CH2:14]N=C=NCC.C1C=CC2N(O)N=NC=2C=1.Cl.Cl.[C:33]([C:37]1C=CC=[CH:39][C:38]=1C1CNCCN1)([CH3:36])([CH3:35])[CH3:34].[CH2:49]([N:51](CC)[CH2:52]C)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:33]([C:37]1[CH:38]=[CH:39][CH:14]=[CH:13][C:12]=1[N:11]1[CH2:10][CH2:52][N:51]([C:6]([CH:2]2[CH2:3][CH2:4][CH2:5][O:1]2)=[O:8])[CH2:49][CH2:20]1)([CH3:36])([CH3:35])[CH3:34]

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 86079(+-)-Tetrahydro-2-furoic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 117621853HCID 117621853, compound

Product 1

HCID 66750896HCID 66750896, compoundYield 59.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To a stirred solution of 2-tetrahydrofuroic acid (23 mg, 0.2 mmol) in DMF (0.5 mL) was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (38 mg, 0.2 mmol) and HOBt (27 mg, 0.2 mmol) in DMF (0.25 mL) followed by 1 (2-(tert-butylphenyl)piperazine dihydrochloride (29 mg, 0.1 mmol) with triethylamine (0.014 mL, 0.2 mmol) in DMF (0.25 mL). After stirring for 15 h at room temperature, saturated sodium hydrogen carbonate solution (1.5 mL) was added to the mixture, and the mixture was extracted with ethyl acetate (2 mL). The organic layer was separated by phase separation filter kit and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in dimethylsulfoxide (1 mL) and the solution was purified by preparative HPLC. The eluted fraction was evaporated by air blowing at 60° C. to give the title compound (18.7 mg, 59%). LC/MS (ESI+) m/z: 317 (M+H)+. purity 100%.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (2 mL)
  2. customThe organic layer was separated by phase separation
  3. filtrationfilter kit
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe resulting residue was dissolved in dimethylsulfoxide (1 mL)
  6. customthe solution was purified by preparative HPLC
  7. customThe eluted fraction was evaporated by air
  8. customblowing at 60° C.

Sources & evidence

ORD record
ord-cb1c03be726d4326a99fbc25a5e6f2a9
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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