Dimethylformamide → HCID 18422127, compound

HRID 1281723Notes

Reaction equation

HRID 1281723 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH:2]1C(O)=O.[NH2:13][C:14]1[CH:15]=[CH:16][C:17]([CH3:37])=[C:18]([NH:20][C:21](=[O:36])[C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:29]3[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]3)[CH:23]=2)[CH:19]=1.CN([CH:41]=[O:42])C>CC(C)=O>[CH3:35][N:32]1[CH2:31][CH2:30][N:29]([CH2:28][C:24]2[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=2)[C:21]([NH:20][C:18]2[CH:19]=[C:14]([NH:13][C:41]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][CH2:3][C:4]=4[CH:9]=3)=[O:42])[CH:15]=[CH:16][C:17]=2[CH3:37])=[O:36])[CH2:34][CH2:33]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 27765552,3-Dihydro-1-benzofuran-2-carboxylic acidHCID 11405006HCID 11405006, compound

Product 1

HCID 18422127HCID 18422127, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2,3-Dihydrobenzofuran-2-carboxylic acid (0.109 g) was added to a stirred mixture of N-(5-amino-2-methylphenyl)-3-(4-methylpiperazin-1-ylmethyl)benzamide (0.15 g), diisopropyethyllamine (0.232 ml), 2-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate(V) (0.253 g) and DMF (10 ml) and the mixture was stirred at ambient temperature for 66 hours. The mixture was partitioned between methylene chloride and water. The organic phase was washed with a saturated aqueous solution of sodium bicarbonate and evaporated. The residue was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Hengoed, Mid-Glamorgan, UK) using a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. The product so obtained was dissolved in acetone and precipitated by the addition of isohexane. There was thus obtained the title compound (0.089 g); NMR Spectrum: (DMSOd6) 2.15 (s, 3H), 2.2 (s, 3H), 2.30-2.45 (m, 8H), 3.25 (t, 2H), 3.55 (s, 2H), 4.6 (t, 2H), 6.85-6.9 (m, 1H), 7.18-7.22 (m, 1H), 7.4-7.66 (m, 3H), 7.75-7.9 (m, 5H), 9.85 (s, 1H), 10.0 (s, 1H); Mass Spectrum: M+H+ 485.

Workup

  1. customThe mixture was partitioned between methylene chloride and water
  2. washThe organic phase was washed with a saturated aqueous solution of sodium bicarbonate
  3. customevaporated
  4. customThe residue was purified by column chromatography on an ion exchange column (isolute SCX column from International Sorbent Technology Limited, Hengoed, Mid-Glamorgan, UK)
  5. additiona 99:1 mixture of methanol
  6. customThe product so obtained
  7. customprecipitated by the addition of isohexane

Sources & evidence

ORD record
ord-ed25c35ff0694240b3890beec0e9a76c
Source dataset
uspto-grants-2002_09
Patent number
US06455520B1

Reaction notes

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