Sodium hydride → HCID 53492705, compound

HRID 2045270Notes

Reaction equation

HRID 2045270 reaction equation
[CH:1]1([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[F:10][C:11]1[CH:12]=[C:13]([CH:18]2[C:27]([CH3:29])([CH3:28])[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:30](O)=[O:31])[CH:24]=3)[NH:19]2)[CH:14]=[C:15]([F:17])[CH:16]=1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[F:10][C:11]1[CH:12]=[C:13]([CH:18]2[C:27]([CH3:28])([CH3:29])[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:30]([NH:7][S:4]([CH:1]4[CH2:3][CH2:2]4)(=[O:6])=[O:5])=[O:31])[CH:24]=3)[NH:19]2)[CH:14]=[C:15]([F:17])[CH:16]=1

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 15765418Cyclopropanesulfonamide2×HCID 67441218HCID 67441218, compound

Product 1

HCID 53492705HCID 53492705, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of cyclopropanesulfonic acid amide (650 mg, 5.36 mmol) in N,N-dimethylformamide (4 mL) was added sodium hydride (210 mg, 5.36 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-(3,5-difluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (210 mg, 0.67 mmol) and 1,1′-carbonyldiimidazole (220 mg, 1.34 mmol) in N,N-dimethylformamide (3 mL) was stirred at 70° C. for 1 h. Then the above suspension of cyclopropanesulfonic acid amide and sodium hydride in N,N-dimethylformamide was added and the mixture was allowed to stir at 25° C. for 1 h. Purification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water) afforded cyclopropanesulfonic acid [2-(3,5-difluoro-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (40 mg, 15%) as a white solid: LC/MS m/e calcd for C21H22F2N2O3S (M+H)+: 421.5, observed: 421.2.

Workup

  1. additionwas added
  2. stirringto stir at 25° C. for 1 h
  3. customPurification by Waters automated flash system (column: Xterra 30 mm×100 mm, sample manager 2767, pump 2525, detector: ZQ mass and UV 2487, solvent system: acetonitrile and 0.1% ammonium hydroxide in water)

Sources & evidence

ORD record
ord-c2da14ed701d4301b9945af2970f89b9
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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