Methanol → HCID 87191081, compound

HRID 2089025Notes

Reaction equation

HRID 2089025 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][C:22]=3[Cl:24])[N:17](S(C3C=CC=CC=3)(=O)=O)[CH:16]=2)[CH:3]=1.CO.[OH-].[Li+]>C1COCC1.O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][C:22]=3[Cl:24])[NH:17][CH:16]=2)[CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 87192433HCID 87192433, compound

Product 1

HCID 87191081HCID 87191081, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 168c (82 mg, 0.164 mmol) in a mixture of 5 mL THF, 5 mL methanol was added a solution of 27 mg (0.654 mmol) lithium hydroxide in 0.5 mL water. After stirring for 16 hours the reaction mixture was concentrated to dryness and the residue suspended in water and a yellow solid was collected by filtration. Purified by silica gel flash chromatography (eluting with 10% ethyl acetate, 90% dichloromethane) provided the title compound as an off-white powder in 51% yield. MS (ESI+) m/z 361.3 (M+H)+; 1H NMR (300 MHz, DMSO-d6) ppm 1.01-1.39 (m, 5H) 1.53-1.65 (m, 1H) 1.66-1.75 (m, 2H) 1.85-1.95 (m, 2H) 3.54-3.69 (m, 1H) 6.51 (s, 1H) 6.60 (s, 1H) 6.79 (d, 1H, J=7.54 Hz) 7.24 (d, 1H, J=5.16 Hz) 7.81 (s, 1H) 8.23 (d, 1H, J=4.76 Hz) 12.41 (bs, 1H).

Workup

  1. concentrationwas concentrated to dryness
  2. filtrationa yellow solid was collected by filtration
  3. customPurified by silica gel flash chromatography (eluting with 10% ethyl acetate, 90% dichloromethane)

Sources & evidence

ORD record
ord-e15f0da3544141909f4ae07d677f6610
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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