Sodium Hydroxide → HCID 16065363, compound

HRID 1991144Notes

Reaction equation

HRID 1991144 reaction equation
[CH:1]1([CH2:7][C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)=[CH:15][N:14](S(C4C=CC=CC=4)(=O)=O)[C:11]3=[N:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[OH-].[Na+]>CCO>[CH:1]1([CH2:7][C:8]2[CH:9]=[C:10]3[C:16]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59128706HCID 59128706, compound

Product 1

HCID 16065363HCID 16065363, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
105 °C

Procedure

A mixture of 97 (25 mg, 0.0575 mmol) and 10% aq. NaOH (0.32 mL) in EtOH (2 mL) was refluxed (oil bath temperature 105° C.) for 30 min., cooled to r.t. and partitioned between water:AcOEt. The aqueous layer was extracted with AcOEt. The extract was dried (MgSO4), concentrated and separated by means of PTLC using AcOEt as eluent to afford desired inhibitor 98 (2.23 mg, 11% over 2 steps) as a solid. 1H NMR (400 MHz; CDCl3) δ 0.86-0.97 (m, 2H), 1.05-1.26 (m, 4H), 1.53-1.73 (m, 5H), 2.54 (d, J=7.1 Hz, 2H), 3.93 (s, 3H), 7.29 (d, J=2.3 Hz, 1H), 7.55 (s, 1H), 7.69 (d, J=0.5 Hz, 1H), 7.74 (d, J=1.9 Hz, 1H), 8.07 (d, J=1.8 Hz, 1H), 9.31 (bs, 1NH); MS (CI) m/z 295 (MH+).

Workup

  1. temperaturecooled to r.t.
  2. custompartitioned between water
  3. extractionThe aqueous layer was extracted with AcOEt
  4. dry with materialThe extract was dried (MgSO4)
  5. concentrationconcentrated
  6. customseparated by means of PTLC
  7. customto afford desired inhibitor 98 (2.23 mg, 11% over 2 steps) as a solid

Sources & evidence

ORD record
ord-066856338ab24ab4906965946b90cd24
Source dataset
uspto-grants-2010_01
Patent number
US07645769B2

Reaction notes

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