Triethylamine → HCID 58333576, compound

HRID 2066889Notes

Reaction equation

HRID 2066889 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][C:16]=3[F:25])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1.[CH3:26][N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH:32]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:26][N:27]1[CH:31]=[CH:30][CH:29]=[C:28]1[CH2:32][N:1]1[CH2:6][CH2:5][CH:4]([O:7][N:8]=[C:9]2[CH2:14][CH2:13][N:12]([C:15]3[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][C:16]=3[F:25])[CH2:11][CH2:10]2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 145041-Methyl-1H-pyrrole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 866550221-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

Product 1

HCID 58333576HCID 58333576, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 63a (24 mg, 0.065 mmol) in 1 mL of DCM, was added 1-methyl-1H-pyrrole-2-carbaldehyde (10.6 g, 0.098 mmol), triethylamine (27 μL, 0.19 mmol) and sodium triacetoxyborohydride (27.6 mg, 0.13 mmol). The mixture was stirred overnight at room temperature, concentrated and purified on preparative HPLC to give 66-1: LC-MS 463.0 (MH+).

Workup

  1. concentrationconcentrated
  2. custompurified on preparative HPLC
  3. customto give 66-1

Sources & evidence

ORD record
ord-c87e000c38be41bc9b806b2e3bd7d6ae
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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