Triethylamine → HCID 69157437, compound

HRID 750348Notes

Reaction equation

HRID 750348 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([S:20]([NH2:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1)[C:6]([C:24](=[O:27])[CH2:25][CH3:26])=[C:5]2[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C.[C:41](=O)([O:47]C(C)(C)C)[O:42][C:43]([CH3:46])([CH3:45])[CH3:44]>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:43]([O:42][C:41](=[O:47])[NH:23][S:20]([C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:7]2[C:6]([C:24](=[O:27])[CH2:25][CH3:26])=[C:5]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([Br:1])[CH:3]=3)[C:8]2=[O:12])=[CH:19][CH:18]=1)(=[O:21])=[O:22])([CH3:46])([CH3:45])[CH3:44]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 69156329HCID 69156329, compound

Product 1

HCID 69157437HCID 69157437, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-(6-bromo-1-oxo-4-phenyl-3-propionyl-1H-isoquinolin-2-ylmethyl)benzenesulfonamide (2.0 g), triethylamine (1.1 ml), 4-dimethylaminopyridine (0.23 g) and methylene chloride (40 ml) was added di-t-butyl carbonate (1.1 ml) at room temperature with stirring, and the mixture was stirred at the same temperature for 1 hr. After the completion of the reaction, the reaction mixture was washed with 1N hydrochloric acid, and the organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by medium pressure preparative LC (hexane/ethyl acetate=3/1-1/1), crystallized from hexane/ethyl acetate=3/1 to give the title compound (2.0 g) in pale-pink crystals. 1H NMR (CDCl3) δ: 0.46 (3H, t, J=6.9 Hz), 1.37 (9H, s), 1.62 (2H, q, J=6.9 Hz), 5.42 (2H, s), 7.14 (1H, br), 7.24-7.30 (2H, m), 7.39 (2H, d, J=8.4 Hz), 7.29-7.51 (4H, m), 7.69 (1H, dd, J=1.8, 8.4 Hz), 7.95 (2H, d, J=8.4 Hz), 8.41 (1H, d, J=8.4 Hz).

Workup

  1. stirringthe mixture was stirred at the same temperature for 1 hr
  2. customAfter the completion of the reaction
  3. washthe reaction mixture was washed with 1N hydrochloric acid
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by medium pressure preparative LC (hexane/ethyl acetate=3/1-1/1)
  7. customcrystallized from hexane/ethyl acetate=3/1

Sources & evidence

ORD record
ord-15e826c4165a4084a1b3f424656ece2f
Source dataset
uspto-grants-2008_07
Patent number
US07402595B2

Reaction notes

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