Methyl Isocyanate → HCID 24821414, compound

HRID 1028467Notes

Reaction equation

HRID 1028467 reaction equation
[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:16]=[C:17]([CH:21]([NH2:23])[CH3:22])[CH:18]=[N:19][CH:20]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[CH3:26][N:27]=[C:28]=[O:29]>C(Cl)Cl>[CH:1]([O:4][C:5]1[CH:25]=[CH:24][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[CH:16]=[C:17]([CH:21]([NH:23][C:28]([NH:27][CH3:26])=[O:29])[CH3:22])[CH:18]=[N:19][CH:20]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 69171564HCID 69171564, compound

Product 1

HCID 24821414HCID 24821414, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 4D (0.32 g, 0.0009 mol) in methylene chloride (15 mL) was added excess methyl isocyanate (0.25 mL) and the mixture was stirred at room temperature for 0.5 hours. After quenching with methanol (10 mL), the solvent was concentrated and the residue was purified on silica gel (75˜100% ethyl acetate in hexane) to give 0.28 g of the title compound (76% yield). 1H NMR (300 MHz, DMSO-d6) 5 ppm 1.29 (d, J=6.25 Hz, 6 H) 1.34 (d, J=6.99 Hz, 3 H) 2.51 (d, J=4.78 Hz, 3 H) 4.55-4.70 (m, 1 H) 4.71-4.85 (m, 1 H) 5.72 (q, J=4.41 Hz, 1 H) 6.48 (d, J=8.09 Hz, 1 H) 6.96-7.07 (m, 2 H) 7.28-7.39 (m, 2 H) 7.77-7.81 (m, 1 H) 7.83 (s, 1 H) 8.42 (d, J=1.84 Hz, 1 H) 8.67 (d, J=2.21 Hz, 1 H). MS (ESI), m/z 413.1 (M+1)+.

Workup

  1. customAfter quenching with methanol (10 mL)
  2. concentrationthe solvent was concentrated
  3. customthe residue was purified on silica gel (75˜100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4eda96b80ad34546bc4e365b05c35a0c
Source dataset
uspto-grants-2014_05
Patent number
US08735595B2

Reaction notes

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