Sodium Hydroxide → HCID 67441940, compound

HRID 2096284Notes

Reaction equation

HRID 2096284 reaction equation
[NH2:1][C:2]1[CH:47]=[CH:46][C:5]([CH2:6][C:7]2[N:12]3[CH:13]=[C:14]([C:16]4[C:24]5[C:19](=[N:20][CH:21]=[CH:22][CH:23]=5)[N:18](S(C5C=CC=CC=5)(=O)=O)[CH:17]=4)[CH:15]=[C:11]3[C:10](=[O:34])[N:9]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:37]=3[O:44][CH3:45])[CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[NH2:1][C:2]1[CH:47]=[CH:46][C:5]([CH2:6][C:7]2[N:12]3[CH:13]=[C:14]([C:16]4[C:24]5[C:19](=[N:20][CH:21]=[CH:22][CH:23]=5)[NH:18][CH:17]=4)[CH:15]=[C:11]3[C:10](=[O:34])[N:9]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:37]=3[O:44][CH3:45])[CH:8]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67442192HCID 67442192, compound

Product 1

HCID 67441940HCID 67441940, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of EXAMPLE 23I (1.7 g, 2.63 mmol) in dioxane (150 ml) was heated with NaOH (0.53 g, 13.2 mmol) at 50° C. for 4 hours. After cooling, the reaction mixture was partitioned between ethyl acetate (300 mL) and brine (200 mL). The organic phase was washed with brine (200 mL), dried over anhydrous Na2SO4, filtered and concentrated. The crude material was purified by flash chromatography (2% methanol in CH2Cl2) to afford the title compound. LC-MS (ESI): m/z 506 (M+H), RT: 1.53 min; 1H NMR (400 MHz, dimethylsulfoxide-d6): δ 3.75 (s, 3H), 3.77 (s, 3H), 3.92 (s, 2H), 4.88 (s, 1H), 4.99 (s, 1H), 6.46 (s, 1H), 6.50 (s, 1H), 6.56 (d, J=8.0 Hz, 3H), 7.07 (d, J=8.4 Hz, 1H), 7.06 (d, J=8 Hz, 2H), 7.14 (d, J=3.2 Hz, 1H), 7.31 (s, 1H), 7.71 (s, 1H), 7.85 (d, J=1.2 Hz, 1H), 8.22 (d, J=8.0 Hz, 1H), 8.26 (d, J=4.8 Hz, 1H), 11.75 (br s, 1H).

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate (300 mL) and brine (200 mL)
  3. washThe organic phase was washed with brine (200 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by flash chromatography (2% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-618d84d3d07649ad9795b1157d2223c9
Source dataset
uspto-grants-2013_05
Patent number
US08450320B2

Reaction notes

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