Dimethylformamide → HCID 86658609, compound

HRID 2045235Notes

Reaction equation

HRID 2045235 reaction equation
[CH3:1][S:2](N)(=[O:4])=[O:3].[H-].[Na+].[CH:8]([NH:11][C:12]([C:14]([NH:17][C:18]1[CH:19]=[C:20]([CH:24]2[C:33]([CH3:35])([CH3:34])[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=C(C(O)=O)[CH:30]=3)[NH:25]2)[CH:21]=[CH:22][CH:23]=1)([CH3:16])[CH3:15])=[O:13])([CH3:10])[CH3:9].[C:39](N1C=CN=C1)([N:41]1C=CN=C1)=[O:40].[CH3:51]N(C)C=O>>[CH:8]([NH:11][C:12](=[O:13])[C:14]([NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]2[C:33]([CH3:34])([CH3:35])[CH2:32][C:31]3[C:26](=[CH:27][CH:28]=[C:1]([S:2]([CH3:51])(=[O:4])=[O:3])[CH:30]=3)[N:25]2[C:39]([NH2:41])=[O:40])[CH:19]=1)([CH3:15])[CH3:16])([CH3:10])[CH3:9]

Participants

6

Reactant 5

HCID 6228Dimethylformamide3×HCID 24758Sodium hydride2×HCID 682631,1'-CarbonyldiimidazoleHCID 72879Methanesulfonamide2×HCID 67440730HCID 67440730, compound

Product 1

HCID 86658609HCID 86658609, compoundYield 21%

Conditions

Temperature
25 °C

Procedure

To a suspension of methanesulfonamide (158 mg, 1.66 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (66 mg, 1.66 mmol). The resulting mixture was stirred at 25° C. for 1 h. A solution of 2-[3-(1-isopropylcarbamoyl-1-methyl-ethylamino)-phenyl]-3,3-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid (100 mg, 0.236 mmol) and 1,1′-carbonyldiimidazole (77 mg, 0.473 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 12 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-isopropyl-2-[3-(6-methanesulfonyl aminocarbonyl-3,3-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamino]-2-methyl-propionamide (25 mg, 21%) as a white solid: LC/MS m/e calcd for C26H36N4O4S (M+H)+: 501.67, observed: 501.1.

Workup

  1. additionwas added
  2. stirringto stir at 25° C. for 12 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-0bf90cb4ecdc43e4b0c728eaeb4dd5a5
Source dataset
uspto-grants-2013_11
Patent number
US08586747B2

Reaction notes

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