Sodium hydride → HCID 58476174, compound

HRID 1801205Notes

Reaction equation

HRID 1801205 reaction equation
[H-].[Na+].[CH:3]1([S:6]([NH2:9])(=[O:8])=[O:7])[CH2:5][CH2:4]1.[CH2:10]([C:12]1[N:16]([C:17]2[CH:18]=[C:19]([CH:23]3[C:32]([CH3:34])([CH3:33])[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:35](O)=[O:36])[CH:29]=4)[NH:24]3)[CH:20]=[CH:21][CH:22]=2)[N:15]=[N:14][N:13]=1)[CH3:11].C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[CH2:10]([C:12]1[N:16]([C:17]2[CH:18]=[C:19]([CH:23]3[C:32]([CH3:33])([CH3:34])[CH2:31][C:30]4[C:25](=[CH:26][CH:27]=[C:28]([C:35]([NH:9][S:6]([CH:3]5[CH2:5][CH2:4]5)(=[O:8])=[O:7])=[O:36])[CH:29]=4)[NH:24]3)[CH:20]=[CH:21][CH:22]=2)[N:15]=[N:14][N:13]=1)[CH3:11]

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 15765418Cyclopropanesulfonamide2×HCID 53492249HCID 53492249, compound

Product 1

HCID 58476174HCID 58476174, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of 60% sodium hydride (160 mg, 3.9 mmol) in N,N-dimethylformamide (1.5 mL) was added cyclopropanesulfonamide (484 mg, 4.0 mmol) at room temperature. The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-[3-(5-ethyl-tetrazol-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (150 mg, 0.4 mmol) and 1,1′-carbonyldiimidazole (136 mg, 0.84 mmol) in N,N-dimethylformamide (2.0 mL) was stirred at 70° C. After stirring at 70° C. for 1 h, the above suspension of cyclopropanesulfonamide 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-ethyl-tetrazol-1-yl)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl}-amide (77 mg, 40%) as a white solid: LC/MS m/e calcd for C24H28N6O3S (M+H)+: 481.59, observed: 481.1.

Workup

  1. stirringAfter stirring at 70° C. for 1 h
  2. additionwas added
  3. stirringto stir at 25° C. for 1 h
  4. 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-f46335d11c8347f08019c92b7c969b81
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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