Triethylamine → tert-butyl {3-[7-({[(4-acetylphenyl)amino] carbonyl}amino)-3-(4-cyanophenyl)-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl]propyl}carbamate

HRID 2039770Notes

Reaction equation

HRID 2039770 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH:7]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[N:8]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]2=[O:12])=[CH:4][CH:3]=1.[C:32]([C:35]1[CH:40]=[CH:39][C:38]([N:41]=[C:42]=[O:43])=[CH:37][CH:36]=1)(=[O:34])[CH3:33].C(N(CC)CC)C>C1C=CC=CC=1>[C:32]([C:35]1[CH:40]=[CH:39][C:38]([NH:41][C:42]([NH:1][C:2]2[CH:11]=[C:10]3[C:5]([CH2:6][CH:7]([C:24]4[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=4)[N:8]([CH2:13][CH2:14][CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]3=[O:12])=[CH:4][CH:3]=2)=[O:43])=[CH:37][CH:36]=1)(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 994524-Acetylphenyl isocyanateHCID 86669320tert-butyl (3-(7-amino-3-(4-cyanophenyl)-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl)propyl)carbamate

Product 1

HCID 86669321tert-butyl {3-[7-({[(4-acetylphenyl)amino] carbonyl}amino)-3-(4-cyanophenyl)-1-oxo-3,4-dihydroisoquinolin-2(1H)-yl]propyl}carbamate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of Intermediate 13 (100 mg, 0.24 mmol) and 10 mL of anhydrous benzene under argon at 25° C. was added 4-acetylphenyl isocyanate (43 mg, 0.26 mmol) and triethylamine (50 mg, 0.48 mmol). The resulting mixture was heated to 100° C. for 12 hours and the reaction was quenched with water. The product was extracted with EtOAc, the layers were separated, and the organic layer was washed with brine, and dried over Na2SO4, and filtered, and concentrated under reduced pressure. The residue was purified by medium pressure liquid chromatography on silica gel using ethyl acetate:hexane (85:15) to yield Intermediate 23 as a light yellow solid.

Workup

  1. customthe reaction was quenched with water
  2. extractionThe product was extracted with EtOAc
  3. customthe layers were separated
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by medium pressure liquid chromatography on silica gel

Sources & evidence

ORD record
ord-dcac7a56112c4f3d98c88d52747eee54
Source dataset
uspto-grants-2013_11
Patent number
US08580817B2

Reaction notes

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