Potassium Carbonate → HCID 90026592, compound

HRID 594877Notes

Reaction equation

HRID 594877 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:11](=[CH:12][CH:13]=1)[O:10][CH2:9][C:6]1([CH2:8][CH2:7]1)[C:5]2([NH:19][C:20]([NH:22][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[S:21])[C:14]([F:18])([F:17])[CH2:15]O.ClC(N(C)C)=C(C)C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]3([C:14]([F:17])([F:18])[CH2:15][S:21][C:20]([NH:22][C:23](=[O:30])[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=4)=[N:19]3)[C:6]3([CH2:7][CH2:8]3)[CH2:9][O:10][C:11]2=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 86724267HCID 86724267, compound

Product 1

HCID 90026592HCID 90026592, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under ice cooling, to a solution of N-{[6-bromo-4-(1,1-difluoro-2-hydroxyethyl)-4H-spiro[chromene-3,1′-cyclopropan]-4-yl]carbamothioyl}benzamide (340 mg, 0.684 mmol) in CH2Cl2 (9 mL) was added 1-chloro-N,N,2-trimethylprop-1-en-1-amine (206 mg, 1.54 mmol), and the mixture was stirred for 17 hours at room temperature. Ice was added and the mixture was neutralized by 10% aqueous K2CO3 and extracted with CH2Cl2. The organic layer was washed with brine and dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography (EtOAc/hexane=1:99-40:60) to afford N-(6′-bromo-5″,5″-difluoro-5″,6″-dihydrodispiro[cyclopropane-1,3′-chromene-4′,4″-[1,3]thiazin]-2″-yl)benzamide (198 mg).

Workup

  1. additionIce was added
  2. extractionextracted with CH2Cl2
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography (EtOAc/hexane=1:99-40:60)

Sources & evidence

ORD record
ord-342322743354467aad8d03490c3c0570
Source dataset
uspto-grants-2016_01
Patent number
US09242973B2

Reaction notes

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