Sodium hydride → HCID 67440912, compound

HRID 1800969Notes

Reaction equation

HRID 1800969 reaction equation
[CH:1]1([S:4]([NH2:7])(=[O:6])=[O:5])[CH2:3][CH2:2]1.[H-].[Na+].[CH3:10][C:11]1([CH3:38])[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:21](O)=[O:22])[CH:18]=2)[NH:13][CH:12]1[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][C:31]([CH3:37])([C:33](=[O:36])[NH:34][CH3:35])[CH3:32])[CH:25]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.CS(N)(=O)=O>CN(C)C=O>[CH:1]1([S:4]([NH:7][C:21]([C:17]2[CH:18]=[C:19]3[C:14](=[CH:15][CH:16]=2)[NH:13][CH:12]([C:24]2[CH:25]=[C:26]([NH:30][C:31]([CH3:37])([CH3:32])[C:33]([NH:34][CH3:35])=[O:36])[CH:27]=[CH:28][CH:29]=2)[C:11]([CH3:38])([CH3:10])[CH2:20]3)=[O:22])(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 72879MethanesulfonamideHCID 15765418CyclopropanesulfonamideHCID 67441278HCID 67441278, compound

Product 1

HCID 67440912HCID 67440912, compoundYield 7.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
25 °C

Procedure

To a suspension of cyclopropanesulfonic acid amide (108 mg, 0.89 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (36 mg, 0.89 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 3,3-dimethyl-2-[3-(1-methyl-1-methylcarbamoyl-ethylamino)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (50 mg, 0.127 mmol) and 1,1′-carbonyldiimidazole (41 mg, 0.253 mmol) in N,N-dimethylformamide (1.5 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 2-[3-(6-cyclopropanesulfonylaminocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-2,N-dimethyl-propionamide (5 mg, 7%) as a white solid: LC/MS m/e calcd for C26H34N4O4S (M+H)+: 499.65, observed: 499.1.

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-e9266af71d8f4ec5a47cfc8cab28982d
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

Loading…