Triethylamine → HCID 59394190, compound

HRID 45068Notes

Reaction equation

HRID 45068 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][C:7]([F:36])([F:35])[C:8]1[CH:9]=[C:10]([NH:14][C:15]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([O:26][C:27]4[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][OH:34])[CH:28]=4)=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)=[O:16])[CH:11]=[CH:12][CH:13]=1.C(N(CC)CC)C>C(Cl)Cl>[F:36][C:7]([F:6])([F:35])[C:8]1[CH:9]=[C:10]([NH:14][C:15]([N:17]2[C:25]3[C:20](=[CH:21][C:22]([O:26][C:27]4[CH:32]=[CH:31][N:30]=[C:29]([CH2:33][O:34][S:2]([CH3:1])(=[O:4])=[O:3])[CH:28]=4)=[CH:23][CH:24]=3)[CH:19]=[CH:18]2)=[O:16])[CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59394062HCID 59394062, compound

Product 1

HCID 59394190HCID 59394190, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methansulfonyl chloride (0.2 mL, 2.46 mmol) is added to a solution of 5-(2-hydroxymethyl-pyridin-4-yloxy)-indole-1-carboxylic acid (3-trifluoromethylphenyl)-amide, Example 25-D, (700 mg, 1.64 mmol) and triethylamine (0.7 mL, 4.92 mmol) in DCM (50 mL) at rt. After 1 h the reaction is partitioned between DCM and saturated aqueous NaHCO3. Organic layer is removed, dried over anhydrous Na2SO4, concentrated and then separated via FCC (EtOAc/heptanes 2:4 to EtOAc/heptanes 9:1) to give the title compound. MS (ESI) m/z 506.0 (M+1).

Workup

  1. customAfter 1 h the reaction is partitioned between DCM and saturated aqueous NaHCO3
  2. customOrganic layer is removed
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customseparated via FCC (EtOAc/heptanes 2:4 to EtOAc/heptanes 9:1)

Sources & evidence

ORD record
ord-b5d0e6804f3d4f7da3249d28ce8ae0bf
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Reaction notes

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