4-Cyanophenyl isocyanate → HCID 131734896, compound

HRID 920845Notes

Reaction equation

HRID 920845 reaction equation
[Si:1]([O:8][CH2:9][CH:10]1[CH2:15][N:14]2[N:16]=[C:17]([I:24])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]2[CH2:12][NH:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:25]([C:28]1[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=1)=[C:26]=[O:27]>C1COCC1>[Si:1]([O:8][CH2:9][CH:10]1[CH2:15][N:14]2[N:16]=[C:17]([I:24])[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:13]2[CH2:12][N:11]1[C:26](=[O:27])[NH:25][C:28]1[CH:29]=[CH:30][C:31]([C:32]#[N:33])=[CH:34][CH:35]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 1703804-Cyanophenyl isocyanateHCID 131734894HCID 131734894, compound

Product 1

HCID 131734896HCID 131734896, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Intermediate 351D (1.2 g, 2.58 mmol) in THF (12 ml) was added 4-isocyanatobenzonitrile (0.446 g, 3.09 mmol) and the solution was stirred at room temperature overnight. The reaction mixture was concentrated and the crude product was purified by silica gel chromatography (40 g REDISEP® column, eluting with 16% EtOAc in hexanes). Fractions containing the product were combined and evaporated to afford Intermediate 351E (0.6 g, 38%) as a white solid. MS(ES): m/z=610 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.32 (s, 1H), 7.75-7.63 (m, 4H), 5.24 (d, J=18.6 Hz, 1H), 4.85-4.77 (m, 1H), 4.47 (d, J=18.6 Hz, 1H), 4.35 (d, J=2.5 Hz, 2H), 4.30-4.22 (m, 2H), 3.73-3.64 (m, 2H), 1.31 (t, J=7.0 Hz, 3H), 0.76-0.71 (m, 9H), −0.04 (m, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe crude product was purified by silica gel chromatography (40 g REDISEP® column, eluting with 16% EtOAc in hexanes)
  3. additionFractions containing the product
  4. customevaporated

Sources & evidence

ORD record
ord-e9532053060a40d3a7df191c523afbc1
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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