Acetic Anhydride → 2-[(4-tert-butylbenzyl)amino]-1-(5-isoquinolinyl)-2-oxoethyl Acetate

HRID 887319Notes

Reaction equation

HRID 887319 reaction equation
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11](=[O:24])[CH:12]([OH:23])[C:13]2[CH:22]=[CH:21][CH:20]=[C:19]3[C:14]=2[CH:15]=[CH:16][N:17]=[CH:18]3)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:27](OC(=O)C)(=[O:29])[CH3:28]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:27]([O:23][CH:12]([C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16][N:17]=[CH:18]2)[C:11]([NH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:26][CH:25]=1)=[O:24])(=[O:29])[CH3:28]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 11291000N-(4-tert-butylbenzyl)-2-hydroxy-2-(5-isoquinolinyl)acetamide

Product 1

HCID 574338442-[(4-tert-butylbenzyl)amino]-1-(5-isoquinolinyl)-2-oxoethyl Acetate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

The product from Example 277B (100 mg, 0.287 mmol) and DMAP (59 mg, 0.480 mmol) in CH2Cl2 (1 mL) was treated with acetic anhydride (38 μL). After stirring for 30 minutes, the mixture was treated with CH2Cl2 (5 mL) and the phases separated. The organic layer was washed with water (10 mL×3), dried (Na2SO4), filtered, and the filtrate was concentrated to provide the title compound. MS (ESI+) m/z 391 (M+H)+; MS (ESI−) m/z 389 (M−H)−; 1H NMR (DMSO, 300 MHz) δ 1.25 (s, 9H), 4.27 (dq, J1 14.9, J2 6.1, 2H), 6.56 (s, 1H), 7.09 (d, J 8.5, 2H), 7.28 (d, J 8.5, 2H), 7.72 (t, J 7.1, 1H), 7.90 (d, J 6.1, 1H), 8.07 (d, J 6.1, 1H), 8.17 (d, J 8.1, 1H), 8.53 (d, J 6.1, 1H), 8.86 (t, J 6.1, 1H), 9.35 (s, 1H);Anal. Calcd for C24H26N2O3+0.8H2O: C, 71.19; H, 6.87; N, 6.92. Found: C, 70.87; H, 6.47; N, 6.92.

Workup

  1. customthe phases separated
  2. washThe organic layer was washed with water (10 mL×3)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cf17c509c76c469ea2b3c1448316668c
Source dataset
uspto-grants-2012_08
Patent number
US08247413B2

Reaction notes

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