Pyridine → HCID 70158888, compound

HRID 1278586Notes

Reaction equation

HRID 1278586 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=3)[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:2].N1C=CC=CC=1.[S:39](Cl)([CH3:42])(=[O:41])=[O:40]>C(Cl)Cl>[CH2:31]([N:3]([CH2:1][CH3:2])[C:4]([C:6]1[CH:7]=[N:8][C:9]([C:12]2([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][S:39]([CH3:42])(=[O:41])=[O:40])[CH:25]=3)[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH3:23])[CH2:20][CH2:21][CH3:22])[CH2:14][CH2:13]2)=[N:10][CH:11]=1)=[O:5])[CH3:32]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 70157266HCID 70157266, compound

Product 1

HCID 70158888HCID 70158888, compoundYield 74.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-[4-(3-Amino-phenyl)-1-(2-methyl-pentyl)-piperidin-4-yl]-pyrimidine-5-carboxylic acid diethylamide (50 mg, 0.114 mmol) and pyridine (0.01 mL, 0.13 mmol) in 5 mL CH2Cl2 at −5° C. was added mesyl chloride (0.01 mL, 0.13 mmol). The reaction warmed to room temperature and stirred 48 hours. The mixture was quenched with NaHCO3 and extracted with CH2Cl2 (3×10 mL). The combined organic layers were dried and concentrated. Purification of the resulting crude material by flash chromatography with 5% MeOH/CH2Cl2 afforded the desired product (44 mg). 1HNMR (400 MHz, CDCl3) δ 8.73 (s, 2H), 7.24-7.17 (comp, 3H), 7.07 (d, 1H), 3.55-3.51 (comp, 2H), 3.33-3.27 (comp, 2H), 3.02-2.94 (comp, 2H), 2.91 (s, 3H), 2.88-2.86 (comp, 2H), 2.45 (br s, 2H), 2.20-2.15 (comp, 4H), 1.68 (br s, 1H), 1.37-1.21 (comp, 10H), 1.05-0.99 (comp, 1H), 0.91-0.83 (comp, 6H); MS (M+1) 516.3.

Workup

  1. customThe mixture was quenched with NaHCO3
  2. extractionextracted with CH2Cl2 (3×10 mL)
  3. customThe combined organic layers were dried
  4. concentrationconcentrated
  5. customPurification of the resulting crude material by flash chromatography with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-f59be0dd6df645c9a5b996f095b85cc3
Source dataset
uspto-grants-2002_09
Patent number
US06444679B1

Reaction notes

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