Pyridine → HCID 76568002, compound

HRID 1728193Notes

Reaction equation

HRID 1728193 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][CH:11]([C:16]([CH3:18])=[CH2:17])[C:10]21[C:26]1[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=1)[NH:20][C:19]2=[O:28].[CH3:29][S:30](Cl)(=[O:32])=[O:31].N1C=CC=CC=1>C(#N)C>[Cl:27][C:23]1[CH:22]=[C:21]2[NH:20][C:19](=[O:28])[C:10]3([CH:9]([C:3]4[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=4[NH:1][S:30]([CH3:29])(=[O:32])=[O:31])[CH2:14][C:13](=[O:15])[NH:12][CH:11]3[C:16]([CH3:18])=[CH2:17])[C:26]2=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 76568135HCID 76568135, compound

Product 1

HCID 76568002HCID 76568002, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of racemic (2′R,3R,4′S)-4′-(2-amino-5-chloro-phenyl)-6-chloro-2′-isopropenylspiro[3H-indole-3,3′-piperidine]-2,6′(1H)-dione (40 mg, 0.1 mmol), methanesulfonyl chloride (0.0092 mL, 0.15 mmol), in acetonitrile (5 mL) was added pyridine (23 mg, 0.3 mmol) at r.t. The reaction mixture was stirred for 4 h. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was separated, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over MgSO4 and concentrated. The residue was purified with Prep. HPLC to give the title compound as a white solid (Yield: 8 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customThe residue was purified with Prep

Sources & evidence

ORD record
ord-e6d82e081582406fbfbf872c7502c119
Source dataset
uspto-grants-2009_02
Patent number
US07495007B2

Reaction notes

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