Water → cis-1-{4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-3-piperidin-1-yl-propan-1-one

HRID 1809070Notes

Reaction equation

HRID 1809070 reaction equation
[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1.[CH2:24]([N:26]([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25].CN([C:34]([O:38]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O.[C:56](#N)C>>[N:1]1([C:11]([C:13]2[CH:17]=[C:16]([CH:18]3[CH2:19][CH2:20][N:21]([C:34](=[O:38])[CH2:25][CH2:24][N:26]4[CH2:29][CH2:30][CH2:56][CH2:28][CH2:27]4)[CH2:22][CH2:23]3)[S:15][CH:14]=2)=[O:12])[C@@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 5

HCID 962WaterHCID 6342AcetonitrileHCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86646702cis-(Octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone

Product 1

HCID 86646706cis-1-{4-[4-(Octahydro-quinoline-1-carbonyl)-thiophen-2-yl]-piperidin-1-yl}-3-piperidin-1-yl-propan-1-one

Procedure

To a solution of cis-(octahydro-quinolin-1-yl)-(5-piperidin-4-yl-thiophen-3-yl)-methanone (CC-033) (0.061 g, 0.18 mmol) in acetonitrile (1 mL) was added triethylamine (0.55 mmol), HATU (0.21 mmol) and 1-piperidinepropionic (0.21 mmol). The reaction mixture was stirred for 4 hours, and then water (1 mL) was added and the resulting solution was purified by HPLC, eluting with 10%-98% acetonitrile in water (containing 20 mM triethylamine). The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.013 g). LCMS m/z 472.00 [M+H]+ RT=7.07 min (Analytical Method 2).

Workup

  1. customthe resulting solution was purified by HPLC
  2. washeluting with 10%-98% acetonitrile in water (containing 20 mM triethylamine)
  3. additionThe fractions containing the desired product
  4. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-840e85afdbaa47a587238cbde4419930
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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