Pyridine → HCID 18373227, compound

HRID 2301833Notes

Reaction equation

HRID 2301833 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([NH:27][C:28](=[O:39])[C:29]2[CH:34]=[CH:33][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:31][CH:30]=2)=[C:6]([CH:26]=1)[C:7]([NH:9][C:10]1[CH:18]=[C:17]2[C:13]([CH:14]=[N:15][N:16]2[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][CH:11]=1)=[O:8].N1C=CC=CC=1.[CH3:46][S:47](Cl)(=[O:49])=[O:48]>ClCCl.C1COCC1>[C:19]([N:16]1[C:17]2[C:13](=[CH:12][CH:11]=[C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:26]=[C:2]([NH:1][S:47]([CH3:46])(=[O:49])=[O:48])[CH:3]=[CH:4][C:5]=3[NH:27][C:28](=[O:39])[C:29]3[CH:30]=[CH:31][C:32]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:34]=3)[CH:18]=2)[CH:14]=[N:15]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 18373154HCID 18373154, compound

Product 1

HCID 18373227HCID 18373227, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirring solution of 5-amino-N-(1-Boc-6-indazolyl)-2-[(4-t-butylbenzoyl)amino]benzamide (144 mg, 0.27 mmol) and pyridine (0.066 mL, 0.82 mmol) in dichloromethane (5 mL) and THF (5 mL) was added methanesulfonyl chloride (0.023 mL, 0.30 mL). After stirring for 24 h, the solvent was removed in vacuo and the residue was dissolved in ethyl acetate and washed with 1 M citric acid, water, satd aq NaHCO3, and brine. The organic phase was then dried with MgSO4, filtered and concentrated in vacuo and the resulting solid was recrystallized from dichloromethane/hexanes to give 137 mg (83%) of tan solid.

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with 1 M citric acid, water
  4. dry with materialThe organic phase was then dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customthe resulting solid was recrystallized from dichloromethane/hexanes

Sources & evidence

ORD record
ord-345e6ee00ca74d6ba9ad12c604066b4f
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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