Acrylic Acid → HCID 11232985, compound

HRID 2192693Notes

Reaction equation

HRID 2192693 reaction equation
[C:1]([NH:5][C:6]1[N:11]=[C:10]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([NH2:21])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[N:8][CH:7]=1)([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl.[C:41](O)(=[O:44])[CH:42]=[CH2:43]>ClCCl.O>[C:1]([NH:5][C:6]1[N:11]=[C:10]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([NH:21][C:41](=[O:44])[CH:42]=[CH2:43])=[CH:20][C:15]=3[N:14]=[CH:13]2)[CH:9]=[N:8][CH:7]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 59783942HCID 59783942, compound

Product 1

HCID 11232985HCID 11232985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[6-(tert-butylamino)pyrazin-2-yl]-1H-benzimidazol-5-amine (20 mg, 0.08 mmol) in anhydrous dichloromethane (2 mL) under N2 was added triethylamine (33 μL, 0.24 mmol), EDAC.HCl (22 mg, 0.12 mmol), 4-(1-pyrrolidino)pyridine (cat.) and acrylic acid (8 μL, 0.12 mmol). The resulting mixture then stirred at RT for 3 clays and was the diluted with H2O (10 mL), the organic phase separated and the aqueous phase extracted with CH2Cl2 (10 mL). The combined organic layers were dried (Na2SO4) and the solvent removed in vacuo. The residue was purified by column chromatography using dichloromethane-methanol (98:2-92:8) as eluant to separate the pure product (10 mg).

Workup

  1. customthe organic phase separated
  2. extractionthe aqueous phase extracted with CH2Cl2 (10 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography
  6. customto separate the pure product (10 mg)

Sources & evidence

ORD record
ord-c4c4d3c17e464a3eb7458d254216c8a1
Source dataset
uspto-grants-2012_12
Patent number
US08329737B2

Reaction notes

Loading…