Acetic Anhydride → HCID 16042512, compound

HRID 545183Notes

Reaction equation

HRID 545183 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:35](=[CH:36][CH:37]=2)[O:34][C:12]2([CH2:17][CH2:16][N:15]([C:18]([C:20]4[CH:29]=[C:28]([O:30][CH3:31])[C:27]5[C:22](=[C:23]([O:32][CH3:33])[CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[O:19])[CH2:14][CH2:13]2)[CH2:11][C:10]3=[O:38])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:39][C:40](OC(C)=O)=[O:41].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:40]([N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[C:9]3[C:35](=[CH:36][CH:37]=2)[O:34][C:12]2([CH2:13][CH2:14][N:15]([C:18]([C:20]4[CH:29]=[C:28]([O:30][CH3:31])[C:27]5[C:22](=[C:23]([O:32][CH3:33])[CH:24]=[CH:25][CH:26]=5)[N:21]=4)=[O:19])[CH2:16][CH2:17]2)[CH2:11][C:10]3=[O:38])[CH2:2][CH2:3]1)(=[O:41])[CH3:39]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67171708HCID 67171708, compound

Product 1

HCID 16042512HCID 16042512, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 165 mg of 6-(piperazin-1-yl)-1′-[(4,8-dimethoxyquinolin-2-yl)carbonyl]spiro[chroman-2,4′-piperidin]-4-one in 2 mL of CHCl3 was added 0.165 mL of Ac2O and 0.33 ml of triethylamine and the mixture was stirred for 4 hrs. The mixture was partitioned between CHCl3 and 1N NaOHaq, and the organic layer was separated, washed with brine, dried over MgSO4, and concentrated. The residue was purified on preparative TLC (SiO2, CHCl3/MeOH=9/1) to afford the intended compound as a yellow powder. 1H-NMR (400 MHz, CDCl3) δ7.74 (1H, d, J=8.4 Hz), 7.45 (1H, ddd, J=8.4, 8.0, 0.8 Hz), 7.32-7.34 (1H, m), 7.18 (1H, dd, J=8.8, 1.4 Hz), 7.16 (1H, s), 7.06 (1H, d, J=8.0 Hz), 6.95 (1H, d, J=8.8 Hz), 4.50-4.60 (1H, m), 4.00-4.20 (1H, m), 4.06 (3H, s), 4.02 (3H, s), 3.70-3.80 (2H, m), 3.50-3.70 (3H, m), 3.33-3.40 (1H, m), 3.00-3.20 (4H, m), 2.78 (1H, d, J=16.8 Hz), 2.72 (1H, d, J=16.8 Hz), 2.21-2.30 (1H, m), 2.10-2.20 (1H, m), 1.70-2.95 (2H, m). MS [M+H]+=559.

Workup

  1. customThe mixture was partitioned between CHCl3 and 1N NaOHaq
  2. customthe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified on preparative TLC (SiO2, CHCl3/MeOH=9/1)

Sources & evidence

ORD record
ord-b648087011fa4adc8ce83c4d8a8711cd
Source dataset
uspto-grants-2011_05
Patent number
US07935712B2

Reaction notes

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