Acrylic Acid → HCID 59783930, compound

HRID 2192691Notes

Reaction equation

HRID 2192691 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([NH2:25])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[N:12][CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[C:33](O)(=[O:36])[CH:34]=[CH2:35]>C1COCC1.O>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([NH:25][C:33](=[O:36])[CH:34]=[CH2:35])[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[N:12][CH:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 6581Acrylic AcidHCID 8471TriethylamineHCID 10449319HCID 10449319, compound

Product 1

HCID 59783930HCID 59783930, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(6-{[(1S)-1-phenylethyl]amino}pyrazin-2-yl)-1H-benzimidazol-6-amine (67 mg, 0.2 mmol) in anhydrous THF (2 mL) under N2 was added triethylamine (67 μl, 0.48 mmol), EDACHCl (46 mg, 0.24 mmol), 4-(1-pyrrolidino)pyridine (cat.) and acrylic acid (17 mg, 0.24 mmol). The resulting mixture then stirred at RT overnight and was the diluted with H2O (10 mL) and the mixture extracted with EtOAc (2×10 mL). The combined organic layers were washed with saturated aqueous Na2CO3, dried (Na2SO4) and the solvent removed in vacuo. The residue was purified by column chromatography using dichloromethane-methanol (98:2-94:6) as eluant to separate the pure product (25 mg).

Workup

  1. extractionthe mixture extracted with EtOAc (2×10 mL)
  2. washThe combined organic layers were washed with saturated aqueous Na2CO3
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by column chromatography
  6. customto separate the pure product (25 mg)

Sources & evidence

ORD record
ord-6b0c6283fef44b438bbdb745dab5f0d4
Source dataset
uspto-grants-2012_12
Patent number
US08329737B2

Reaction notes

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