m-Chloroperbenzoic acid → HCID 57541250, compound

HRID 421749Notes

Reaction equation

HRID 421749 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH3:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[C:20]3[C:28](=[O:29])[C:27]4[CH:30]=[C:31]([CH2:34][S:35]([NH:38][CH2:39][C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][N:41]=5)(=[O:37])=[O:36])[CH:32]=[CH:33][C:26]=4[CH:25]=[CH:24][C:21]3=[N:22][CH:23]=2)[CH:15]=[N:14]1.C(=O)([O-])O.[Na+]>ClCCl>[CH3:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[C:20]3[C:28](=[O:29])[C:27]4[CH:30]=[C:31]([CH2:34][S:35]([NH:38][CH2:39][C:40]5[CH:45]=[CH:44][CH:43]=[CH:42][N+:41]=5[O-:6])(=[O:36])=[O:37])[CH:32]=[CH:33][C:26]=4[CH:25]=[CH:24][C:21]3=[N:22][CH:23]=2)[CH:15]=[N:14]1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 45142457MK-8033

Product 1

HCID 57541250HCID 57541250, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Chloroperoxybenzoic acid (26.1 mg, 0.106 mmol) was added to a solution of 1-[3-(1-methyl-1H-pyrazol-4-yl)-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl]-N-(pyridin-2-ylmethyl)methanesulfonamide (50 mg, 0.106 mmol) in dichloromethane (1.06 mL) at 0 C. After 15 min., the reaction was allowed to warm to room temperature and stirring was continued for 6 hr. Then, aqueous sodium hydrogen carbonate (saturated, 50 mL) was added, and the mixture was extracted with dichloromethane (3×50 mL). The combined organic extracts were washed with aqueous sodium hydrogen carbonate (saturated, 2×75 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative HPLC Reverse phase (C-18), eluting with Acetonitrile/Water+0.05% TFA, to afford the title compound as a yellow solid. 1H NMR (600 MHz, DMSO-D6) δ 9.21 (d, 1H); 8.53 (d, 1H); 8.47 (s, 1H); 8.25 (d, 1H); 8.17 (s, 1H); 8.14 (s, 1H); 7.80 (m, 3H); 7.46 (d, 1H); 7.40 (d, 1H); 7.34 (m, 3H); 4.71 (s, 2H); 4.27 (d, 2H); 3.88 (s, 3H). LRMS (APCI) calculated for C25H21N5O4S [M+H]+, 488.1; found 488.1.

Workup

  1. waitwas continued for 6 hr
  2. extractionthe mixture was extracted with dichloromethane (3×50 mL)
  3. washThe combined organic extracts were washed with aqueous sodium hydrogen carbonate (saturated, 2×75 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by preparative HPLC Reverse phase (C-18)
  7. washeluting with Acetonitrile/Water+0.05% TFA

Sources & evidence

ORD record
ord-c18a75370dba4a61b5e30ab2831cb7f6
Source dataset
uspto-grants-2012_01
Patent number
US08101603B2

Reaction notes

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