HCID 86688113, compound → HCID 67469772, compound

HRID 407976Notes

Reaction equation

HRID 407976 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][C@H:13]1[CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH:20]2[CH2:25][CH2:24][N:23](C(OC(C)(C)C)=O)[CH2:22][CH2:21]2)[C:14]1=[O:33]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[NH:12][C@H:13]1[CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[C:14]1=[O:33]

Participants

3

Reactant 1

HCID 86688113HCID 86688113, compound

Product 1

HCID 67469772HCID 67469772, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A solution of (S)-tert-butyl 4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxoazepan-1-yl)piperidine-1-carboxylate (1.0 g, 2.0 mmol) in 50% TFA/DCM was stirred a ambient temperature for 1 hour. The mixture was concentrated in vacuo. 1N NaOH (100 mL) was added to the residue and the product was extracted into DCM (2×50 mL). The combined organic layers were dried over MgSO4, filtered and concentrated in vacuo to give (S)-3-(2-fluoro-4-(methylsulfonyl)phenylamino)-1-(piperidin-4-yl)azepan-2-one (0.4 g, 1 mmol, 50%).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. addition1N NaOH (100 mL) was added to the residue
  3. extractionthe product was extracted into DCM (2×50 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b48a719323d04997b126f3171a271c4a
Source dataset
uspto-grants-2014_06
Patent number
US08754226B2

Reaction notes

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