Sodium hydride → HCID 53491694, compound

HRID 1801011Notes

Reaction equation

HRID 1801011 reaction equation
[CH3:1][S:2]([NH2:5])(=[O:4])=[O:3].[H-].[Na+].[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:27](O)=[O:28])[CH:21]=3)[NH:16]2)=[CH:11][C:10]=1[N:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1.C(N1C=CN=C1)(N1C=CN=C1)=O>CN(C)C=O>[F:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:24]([CH3:26])([CH3:25])[CH2:23][C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:27]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[O:28])[CH:21]=3)[NH:16]2)=[CH:11][C:10]=1[N:30]1[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 72879Methanesulfonamide2×HCID 674410266-Quinolinecarboxylic acid, 2-[4-fluoro-3-(4-morpholinyl)phenyl]-1,2,3,4-tetrahydro-3,3-dimethyl-

Product 1

HCID 53491694HCID 53491694, compoundYield 25.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of methanesulfonamide (150 mg, 1.55 mmol) in N,N-dimethylformamide (3 mL) was added sodium hydride (62 mg, 1.55 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-(4-fluoro-3-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (120 mg, 0.31 mmol) and 1,1′-carbonyldiimidazole (100 mg, 0.62 mmol) in N,N-dimethylformamide (3 mL) was stirred at 70° C. for 1 h. Then the above suspension of methanesulfonamide 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 N-[2-(4-fluoro-3-morpholin-4-yl-phenyl)-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carbonyl]-methanesulfonamide (36 mg, 25%) as a white solid: LC/MS m/e calcd for C23H28FN3O4S (M+H)+: 462.6, observed: 462.4.

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-c654c82dee8a49178097b9467749908c
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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