Benzoic Acid → HCID 57513868, compound

HRID 2262721Notes

Reaction equation

HRID 2262721 reaction equation
[CH:1]1([N:5]2[CH2:10][CH2:9][N:8]([C:11](=[O:19])[CH2:12][N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[CH2:7][CH2:6]2)[CH2:4][CH2:3][CH2:2]1.[C:20](O)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C1(C)C=CC=CC=1>CC(N(C)C)=O.C(#N)C>[C:20]([N:16]1[CH2:15][CH2:14][N:13]([CH2:12][C:11]([N:8]2[CH2:9][CH2:10][N:5]([CH:1]3[CH2:2][CH2:3][CH2:4]3)[CH2:6][CH2:7]2)=[O:19])[CH2:18][CH2:17]1)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 243Benzoic AcidHCID 1140TolueneHCID 57442330HCID 57442330, compound

Product 1

HCID 57513868HCID 57513868, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
50 °C

Procedure

Dissolve 1-cyclobutyl-4-(piperazin-1-ylacetyl)piperazine (32 mg, 0.12 mmol) and benzoic acid (17.6 mg, 0.14 mmol) in dry DMA (0.75 mL), TEA (0.033 mL, 0.24 mmol) and toluene (0.75 mL). Add a solution of DMC (41 mg, 27.3 mmol) in acetonitrile (1.2 mL). Heat the mixture at 50° C. for 3 h. Cool and concentrate. Partition the residue between EtOAc (10 mL) and 1 N NaOH (10 mL). Extract the organic phase and place directly on an SCX ion exchange resin cartridge. Wash the resin first with EtOAc (4 mL). Discard this wash. Second, wash the resin with EtOAC/MeOH/TEA (10/1/1). Collect this wash and evaporate to yield the title compound. 1H NMR (CDCl3). δ 7.41-7.39 (m, 5H), 6.89 (d, 1H), 3.86-3.78 (m, 2H), 3.63-3.57 (m, 4H), 3.44-3.40 (m, 2H), 3.23 (s, 2H), 2.74-2.66 (m, 1H), 2.6-2.43 (m, 4H) 2.33-2.26 (m, 4H), 2.08-2.00 (m, 2H), 1.90-1.84 (m, 2H), 1.76-1.70 (m, 2H); LC-MS (M+1) 371.02.

Workup

  1. temperatureCool
  2. concentrationconcentrate
  3. customPartition the residue between EtOAc (10 mL) and 1 N NaOH (10 mL)
  4. extractionExtract the organic phase and place directly on an SCX ion exchange resin cartridge
  5. washWash the resin first with EtOAc (4 mL)
  6. washSecond, wash the resin with EtOAC/MeOH/TEA (10/1/1)
  7. customCollect
  8. washthis wash
  9. customevaporate

Sources & evidence

ORD record
ord-0872e8fc773d4eb5b1cbe8e95c05cac8
Source dataset
uspto-grants-2010_12
Patent number
US07851474B2

Reaction notes

Loading…