Phenyl isocyanate → HCID 44514436, compound

HRID 1011642Notes

Reaction equation

HRID 1011642 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:13]1([C:26]2[NH:27][C:28]3[C:33]([C:34]=2[CH3:35])=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:18][CH2:17][C:16]([N:23]([CH3:25])[CH3:24])([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][CH2:14]1.[C:36]1([N:42]=[C:43]=[O:44])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>C(#N)C.[OH-].[Na+]>[CH2:19]([C:16]1([N:23]([CH3:25])[CH3:24])[CH2:17][CH2:18][C:13]([C:5]2[NH:6][C:7]3[C:12]([C:4]=2[CH2:3][CH2:2][NH:1][C:43]([NH:42][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:44])=[CH:11][CH:10]=[CH:9][CH:8]=3)([C:26]2[NH:27][C:28]3[C:33]([C:34]=2[CH3:35])=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:14][CH2:15]1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 44514152HCID 44514152, compound

Product 1

HCID 44514436HCID 44514436, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 14798Sodium HydroxideSolvent

Procedure

4-(3-(2-aminoethyl)-1H-indol-2-yl)-1-butyl-N,N-dimethyl-4-(3-methyl-1H-indol-2-yl)cyclohexylamine (120 mg, 0.255 mmol, mixture of the two possible diastereoisomers in a ratio of approx. 30:70) was mixed in acetonitrile (2.4 ml) with phenyl isocyanate (0.042 ml, 0.386 mmol). After a reaction time of 2 h at 24° C. the reaction mixture was diluted with 1N sodium hydroxide solution (20 ml) and extracted with dichloromethane (4×10 ml). The combined organic phases were dried with Na2SO4 and then filtered. The volatile constituents of the filtrate were completely removed in a vacuum. The residue (yellow solid, 150 mg) was purified by column chromatography [silica gel 60 (25 g); cyclohexane/ethyl acetate 2:1 (300 ml), ethyl acetate/methanol 1:1 (300 ml]. The product was obtained as a white solid with a yield of 115 mg (76%) (melting point 115-120° C., mixture of the two possible diastereoisomers in a ratio of approx. 25:75).

Workup

  1. extractionextracted with dichloromethane (4×10 ml)
  2. dry with materialThe combined organic phases were dried with Na2SO4
  3. filtrationfiltered
  4. customThe volatile constituents of the filtrate were completely removed in a vacuum
  5. customThe residue (yellow solid, 150 mg) was purified by column chromatography [silica gel 60 (25 g)
  6. customThe product was obtained as a white solid with a yield of 115 mg (76%) (
  7. additionmelting point 115-120° C., mixture of the two possible diastereoisomers in a ratio of approx. 25:75)

Sources & evidence

ORD record
ord-82cdfa4f1357499e9a926a3848a9171b
Source dataset
uspto-grants-2011_07
Patent number
US07977370B2

Reaction notes

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