HCID 59542474, compound → HCID 59542542, compound

HRID 1809095Notes

Reaction equation

HRID 1809095 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[O:20])[CH:18]=2)[CH2:9]1)=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[N:21]1([C:19]([C:17]2[CH:18]=[C:14]([CH:10]3[CH2:11][CH2:12][CH2:13][NH:8][CH2:9]3)[S:15][CH:16]=2)=[O:20])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

3

Reactant 1

HCID 59542474HCID 59542474, compound

Product 1

HCID 59542542HCID 59542542, compoundYield 105.8%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3-[4-(Azepane-1-carbonyl)-thiophen-2-yl]-piperidine-1-carboxylic acid tert-butyl ester (0.066 g) was dissolved in TFA/DCM (1:1, 5 mL) and stirred for 1 hour. The solvent was then evaporated and the residue dissolved in DCM and purified using a SCX-2 column. After washing with methanol and acetonitrile, the desired compound was washed from the column with ammonia (2 M in MeOH). Evaporation gave the title compound as a clear colourless oil (0.052 g). LCMS m/z 293.14 [M+H]+ RT=5.27min (Analytical Method 2). 1H NMR δ (ppm)(CHCl3-d): 7.3 (s, 1H), 6.9 (s, 1H), 3.8 (m, 2H), 3.5 (m, 2H), 3.3 (d, 1H), 3.1 (d, 1H), 2.9 (m, 1H), 2.7-2.6 (m, 3H), 2.1 (m, 1H), 1.8-1.5 (m, 11H).

Workup

  1. customThe solvent was then evaporated
  2. dissolutionthe residue dissolved in DCM
  3. custompurified
  4. washAfter washing with methanol and acetonitrile
  5. washthe desired compound was washed from the column with ammonia (2 M in MeOH)
  6. customEvaporation

Sources & evidence

ORD record
ord-30aadc6ca4604a9db17812e339334fef
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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