Phenyl isocyanate → HCID 69331787, compound

HRID 2370931Notes

Reaction equation

HRID 2370931 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[C:11]([C:13]([CH2:22][C:23]3[CH:24]=[N:25][C:26]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:27][CH:28]=3)([C:18]([O:20][CH3:21])=[O:19])[C:14]([O:16][CH3:17])=[O:15])[N:10]=[CH:9]2)=[CH:4][CH:3]=1.[C:37]1([N:43]=[C:44]=[O:45])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1.C(N(CC)CC)C>C(#N)C.CN(C)C1C=CN=CC=1>[C:33]([O:32][C:30]([NH:29][C:26]1[N:25]=[CH:24][C:23]([CH2:22][C:13]([C:11]2[N:10]=[CH:9][N:8]([C:5]3[CH:4]=[CH:3][C:2]([NH:1][C:44]([NH:43][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[O:45])=[CH:7][CH:6]=3)[CH:12]=2)([C:14]([O:16][CH3:17])=[O:15])[C:18]([O:20][CH3:21])=[O:19])=[CH:28][CH:27]=1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

Participants

6

Reactant 3

HCID 7672Phenyl isocyanateHCID 8471TriethylamineHCID 69331502HCID 69331502, compound

Product 1

HCID 69331787HCID 69331787, compoundYield 76.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

50 mg (0.10 mmol) of the compound from example 12f were dissolved in 10 ml of acetonitrile. The resulting solution was cooled to 0° C., and 14 mg (0.12 mmol, 13.2 μl) of phenyl isocyanate and 20 mg (0.20 mmol, 28 μl) of triethylamine were added. The mixture was warmed to RT, and a spatula tip of 4-dimethylaminopyridine was added. The reaction mixture was left to stand overnight and then evaporated, and the residue was chromatographed on silica gel. 47 mg of the title compound were obtained.

Workup

  1. temperatureThe mixture was warmed to RT
  2. waitThe reaction mixture was left
  3. customevaporated
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-1773df9ff0324a46bfaef0378ba84381
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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