Sodium hydride → HCID 53492707, compound

HRID 2045276Notes

Reaction equation

HRID 2045276 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:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][C:12]=1[CH:23]1[C:32]([CH3:34])([CH3:33])[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:35](O)=[O:36])[CH:29]=2)[NH:24]1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:13][C:12]=1[CH:23]1[C:32]([CH3:33])([CH3:34])[CH2:31][C:30]2[C:25](=[CH:26][CH:27]=[C:28]([C:35]([NH:7][S:4]([CH:1]3[CH2:3][CH2:2]3)(=[O:6])=[O:5])=[O:36])[CH:29]=2)[NH:24]1

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 15765418Cyclopropanesulfonamide2×HCID 534927062-(2-Fluoro-5-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid

Product 1

HCID 53492707HCID 53492707, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of cyclopropanesulfonic acid amide (78.7 mg, 0.65 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (26 mg, 0.65 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-(2-fluoro-5-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (50 mg, 0.13 mmol) and 1,1′-carbonyldiimidazole (42 mg, 0.26 mmol) in N,N-dimethylformamide (2 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-(2-fluoro-5-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-amide (19 mg, 30%) as a white solid: LC/MS m/e calcd for C25H30FN3O4S (M+H)+: 488.6, observed: 488.4.

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-cf37c0970d9d4fbaa138c3f0bfe17453
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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