Ethyl isocyanate → HCID 21865576, compound

HRID 857292Notes

Reaction equation

HRID 857292 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH2:12][C:13]2[CH:14]=[C:15]([C:19]3[CH:20]=[C:21]([C:29]([CH3:33])([CH3:32])[C:30]#[N:31])[CH:22]=[C:23]4[C:28]=3[N:27]=[CH:26][CH:25]=[CH:24]4)[CH:16]=[CH:17][CH:18]=2)=[CH:7][CH:6]=1)(=O)=O.C1CCN2C(=NCCC2)CC1.[CH2:45]([N:47]=[C:48]=[O:49])[CH3:46]>C1COCC1.C([O-])(O)=O.[Na+]>[C:30]([C:29]([CH3:33])([CH3:32])[C:21]1[CH:22]=[C:23]2[C:28](=[C:19]([C:15]3[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=3)[CH2:12][N:11]([C:8]3[CH:9]=[CH:10][C:5]([S:2][CH3:1])=[CH:6][CH:7]=3)[C:48]([NH:47][CH2:45][CH3:46])=[O:49])[CH:20]=1)[N:27]=[CH:26][CH:25]=[CH:24]2)#[N:31]

Participants

6

Reactant 3

HCID 8022Ethyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21865597HCID 21865597, compound

Product 1

HCID 21865576HCID 21865576, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

To solution of 2-(8-{3-[(4-methanesulfonyl-phenylamino)-methyl]-phenyl}-quinolin-6-yl)-2-methyl-propionitrile from EXAMPLE 36 (Step 1) (1.0 eq) in 2 mL of THF (0.17M) was added DBU (1.1 eq) and ethyl-isocyanate (8.3 eq). The resulting mixture was stirred at 60° C. for 12 h, poured in saturated aqueous NaHCO3 and extracted with EtOAc (2×). The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. Flash chromatography (CH2Cl2:EtOAc; 4:1) afforded a contaminated sample of the desired compound as a oil. It was used as such in the next step.

Workup

  1. extractionextracted with EtOAc (2×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-94f585a81412449092c3707eb2940b22
Source dataset
uspto-grants-2006_12
Patent number
US07144896B2

Reaction notes

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