Sodium Carbonate → HCID 11562043, compound

HRID 1992404Notes

Reaction equation

HRID 1992404 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH2:14][N:15]2[CH2:22][CH:21]3[O:23][CH:17]([CH2:18][NH:19][CH2:20]3)[CH2:16]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[CH3:24][N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27]([CH:34]=O)=[CH:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[Na+].[Na+]>ClCCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][CH2:13][CH2:14][N:15]2[CH2:22][CH:21]3[O:23][CH:17]([CH2:18][N:19]([CH2:34][C:27]4[C:28]5[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=5)[N:25]([CH3:24])[CH:26]=4)[CH2:20]3)[CH2:16]2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 878941-Methyl-1H-indole-3-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 685189574-cyano-N-[2-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)ethyl]-benzenesulfonamide

Product 1

HCID 11562043HCID 11562043, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 4-cyano-N-[2-(9-oxa-3,7-diaza-bicyclo[3.3.1]non-3-yl)-ethyl]-benzenesulfonamide (0.101 g, 0.30 mmol) and 1-methyl-1H-indole-3-carbaldehyde (0.081 g, 0.51 mmol) in 1,2-dichloroethane (4 mL) was agitated for 1.5 hours at room temperature. Sodium triacetoxyborohydride (0.216 g, 1.02 mmol) was added and resulting mixture was agitated over night at room temperature. An aqueous solution of Na2CO3 (3 mL) was added and the aqueous layer was extracted with dichloromethane (3×4 mL). The combined organic layers were concentrated in vacuo and the crude product was purified by chromatography on silica gel using methanol saturated with ammonia in dichloromethane as eluent, which afforded 76 mg (52.8%) of the title compound.

Workup

  1. customresulting mixture
  2. stirringwas agitated over night at room temperature
  3. extractionthe aqueous layer was extracted with dichloromethane (3×4 mL)
  4. concentrationThe combined organic layers were concentrated in vacuo
  5. customthe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-61ae9431537d42e7931650173a6d0410
Source dataset
uspto-grants-2010_01
Patent number
US07648985B2

Reaction notes

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