Sodium Carbonate → HCID 86655023, compound

HRID 2066891Notes

Reaction equation

HRID 2066891 reaction equation
C(=O)(O)[O-].[Na+].[NH:6]1[CH2:11][CH2:10][CH:9]([O:12][N:13]=[C:14]2[CH2:19][CH2:18][N:17]([C:20]3[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][C:21]=3[F:30])[CH2:16][CH2:15]2)[CH2:8][CH2:7]1.[N:31]#[C:32]Br.C(=O)([O-])[O-].[Na+].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C(Cl)Cl.O>[F:30][C:21]1[CH:22]=[C:23]([S:26]([CH3:29])(=[O:27])=[O:28])[CH:24]=[CH:25][C:20]=1[N:17]1[CH2:18][CH2:19][C:14](=[N:13][O:12][CH:9]2[CH2:10][CH2:11][N:6]([C:32]#[N:31])[CH2:7][CH2:8]2)[CH2:15][CH2:16]1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 10476Cyanogen BromideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516892Sodium BicarbonateHCID 866550221-(2-Fluoro-4-methanesulfonyl-phenyl)-piperidin-4-one O-piperidin-4-yl-oxime

Product 1

HCID 86655023HCID 86655023, compoundYield 135.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To sodium bicarbonate (34 mg, 0.4 mmol), was added water (17 μL) and 63a (74 mg, 0.2 mmol) in 1 mL of DCM. The mixture was cooled to 0° C. and cyanogen bromide (25 mg, 0.24 mmol) was added. The mixture was stirred at room temperature overnight. Sodium carbonate was added as well as magnesium sulfate and the solids were filtered and rinsed with DCM. The filtrate was concentrated to give 107 mg of 68b.

Workup

  1. filtrationthe solids were filtered
  2. washrinsed with DCM
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8ba083ad998d4497a42915e08918ce7a
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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