Potassium trimethylsilanolate → HCID 178504667, compound

HRID 2401149Notes

Reaction equation

HRID 2401149 reaction equation
C[Si](C)(C)[O-].[K+].[Cl:7][C:8]1[CH:9]=[C:10]2[NH:32][C:31]([O:33][C@H:34]3[CH2:39][CH2:38][C@H:37]([C:40]([O:42]CC)=[O:41])[CH2:36][CH2:35]3)=[N:30][C:11]2=[N:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1>O1CCCC1>[Cl:7][C:8]1[CH:9]=[C:10]2[NH:32][C:31]([O:33][C@H:34]3[CH2:35][CH2:36][C@H:37]([C:40]([OH:42])=[O:41])[CH2:38][CH2:39]3)=[N:30][C:11]2=[N:12][C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:22][CH:21]=2)=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 178472483HCID 178472483, compound

Product 1

HCID 178504667HCID 178504667, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Potassium trimethylsilanolate (278 mg, 2.16 mmol) was added to a tetrahydrofuran (3 mL) solution of ethyl trans-4-({6-chloro-5-[4′-(methylsulfonyl)biphenyl-4-yl]-1H imidazo[4,5-b]pyridin-2-yl}oxy)cyclohexanecarboxylate (240 mg, 0.43 mmol), and the mixture was stirred at rt for 16 h. The reaction mixture was partitioned between EtOAc and 10% aqueous citric acid. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated. Trituration of the resulting crude product with acetonitrile (10 mL) provided the title compound as an off-white solid. LC-MS: calculated for C26H24ClN3O5S 526.0, observed m/e: 526.3 (M+H)+ (Rt 0.8/2 min). 1H NMR δ (ppm) (DMSO-d6): 8.03-7.99 (5 H, m), 7.86 (2 H, d, J=8.16 Hz), 7.79 (2 H, d, J=8.12 Hz), 5.01-4.97 (1 H, m), 2.30 (1 H, m), 2.24 (3 H, d, J=10.17 Hz), 2.00 (3 H, m), 1.58-1.49 (4 H, m).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and 10% aqueous citric acid
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-a5d2813a6d174a37ae7b3d918341b242
Source dataset
uspto-grants-2014_08
Patent number
US08796258B2

Reaction notes

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