Nitrogen → HCID 66816324, compound

HRID 1754946Notes

Reaction equation

HRID 1754946 reaction equation
Br[C:2]1[S:6][C:5]([S:7]([N:10]2[CH2:30][CH2:29][C:13]3([N:17]=[C:16]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=4)[NH:15][C:14]3=[O:28])[CH2:12][CH2:11]2)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[CH3:31][N:32]([CH3:44])[C:33]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)=[O:34].C([O-])([O-])=O.[Na+].[Na+].N#N>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.CCO>[CH3:31][N:32]([CH3:44])[C:33](=[O:34])[C:35]1[CH:36]=[CH:37][C:38]([C:2]2[S:6][C:5]([S:7]([N:10]3[CH2:11][CH2:12][C:13]4([N:17]=[C:16]([C:18]5[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:27])[F:26])[CH:19]=5)[NH:15][C:14]4=[O:28])[CH2:29][CH2:30]3)(=[O:8])=[O:9])=[CH:4][CH:3]=2)=[CH:39][CH:40]=1

Participants

9

Reactant 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 35037674-(Dimethylcarbamoyl)phenylboronic AcidHCID 49838533HCID 49838533, compound

Product 1

HCID 66816324HCID 66816324, compoundYield 77.5%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 8-(5-bromo-thiophene-2-sulfonyl)-2-(3-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (11.1 mg, 0.0212 mmol), 4-(N,N-dimethylaminocarbonyl)phenylboronic acid (8.0 mg, 0.041 mmol), Pd(PPh3)4 (3.8 mg, 0.0033 mmol) and Na2CO3 (22.0 mg, 0.208 mmol) in toluene (0.12 ml)-EtOH (0.12 ml)-H2O (0.12 ml) was stirred at 85° C. for 20 hours in a sealed test tube in an N2 atmosphere. The reaction mixture was cooled to room temperature and extracted with AcOEt. The organic layer was washed with a saturated aqueous NH4Cl solution, and then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (AcOEt) to give N,N-dimethyl-4-{5-[4-oxo-2-(3-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-thiophen-2-yl}-benzamide (9.7 mg, 77%).

Workup

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with a saturated aqueous NH4Cl solution
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (AcOEt)

Sources & evidence

ORD record
ord-4b1ff05762fe4dfe90eff7fb172e5048
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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