Acrylic Acid → HCID 11416425, compound

HRID 2192692Notes

Reaction equation

HRID 2192692 reaction equation
[C:1]([NH:5][C:6]1[N:11]=[C:10]([N:12]2[C:16]3[CH:17]=[C:18]([NH2:21])[CH:19]=[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]=[C:18]([NH:21][C:41](=[O:44])[CH:42]=[CH2:43])[CH:19]=[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 597839241-[6-[(1,1-Dimethylethyl)amino]-2-pyrazinyl]-1H-benzimidazol-6-amine

Product 1

HCID 11416425HCID 11416425, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-[6-(tert-butylamino)pyrazin-2-yl]-1H-benzimidazol-6-amine (22 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 days 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 (98:2-93:7) 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-2c8eb6f3417a4bae8cc91c52ef65b588
Source dataset
uspto-grants-2012_12
Patent number
US08329737B2

Reaction notes

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