Phenyl isocyanate → HCID 178521947, compound

HRID 2383479Notes

Reaction equation

HRID 2383479 reaction equation
[Cl-].[Br:2][C:3]1[C:15]2[C:14]3[CH2:13][CH2:12][NH2+:11][CH2:10][C:9]=3[CH:8]=[N:7][C:6]=2[NH:5][N:4]=1.CCN(C(C)C)C(C)C.[C:25]1([N:31]=[C:32]=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>ClCCl>[Br:2][C:3]1[C:15]2[C:14]3[CH2:13][CH2:12][N:11]([C:32]([NH:31][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[O:33])[CH2:10][C:9]=3[CH:8]=[N:7][C:6]=2[NH:5][N:4]=1

Participants

5

Reactant 3

HCID 7672Phenyl isocyanateHCID 81531DiisopropylethylamineHCID 178419489HCID 178419489, compound

Product 1

HCID 178521947HCID 178521947, compoundYield 293.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-bromo-6,7,8,9-tetrahydro-3H-pyrazolo[3,4-c][2,7]naphthyridin-7-ium chloride (0.16 g, 0.55 mmol) in dichloromethane (5 mL), Hunig's Base (0.59 mL, 3.3 mmol) was added and stirred under inert atmosphere. After 10 minutes, phenyl isocyanate (0.06 mL, 0.57 mmol) was added and the reaction was allowed to stir at room temperature for 2 hours. The mixture was diluted with dichloromethane (10 mL) and washed with water (2×5 mL), dried over anhydrous sodium sulfate, filtered and dried in vacuo. The resulting pale brown solid was purified by flash column chromatography (SiO2, 50% ethyl acetate in hexanes) to give the desired product as light pink solid (0.6 g, 30%). M.p.=249-250° C., 400 MHz 1H NMR (DMSO-d6) δ: 10.64 (s, 1H), 9.66 (s, 1H), 8.82 (s, 1H), 8.25 (s, 1H), 7.90 (d, J=7.6 Hz, 1H), 7.68 (d, J=8.8 Hz, 2H), 7.2 (d, J=8.8 Hz, 2H), 7.07 (t, J=7.2 Hz, 1H), 6.95 (d, J=6.4 Hz, 1H), 4.25 (t, J=5.2 Hz, 2H), 3.24 (s, 2H), 2.96 (t, J=6 Hz, 2H), 2.2-2.14 (m, 2H); LCMS [M+H]: 350.

Workup

  1. stirringto stir at room temperature for 2 hours
  2. washwashed with water (2×5 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customdried in vacuo
  6. customThe resulting pale brown solid was purified by flash column chromatography (SiO2, 50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1baeddf74d8f4c669e275fa5793129f1
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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