Decahydroquinoline → HCID 86646712, compound

HRID 1914551Notes

Reaction equation

HRID 1914551 reaction equation
[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([OH:9])=O)[CH:3]=1.[NH:10]1[CH:19]2[CH:14]([CH2:15][CH2:16][CH2:17][CH2:18]2)[CH2:13][CH2:12][CH2:11]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[Br:1][C:2]1[S:6][CH:5]=[C:4]([C:7]([N:10]2[C@@H:19]3[C@@H:14]([CH2:15][CH2:16][CH2:17][CH2:18]3)[CH2:13][CH2:12][CH2:11]2)=[O:9])[CH:3]=1

Participants

5

Reactant 3

HCID 92911DecahydroquinolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 120399785-Bromothiophene-3-carboxylic acid

Product 1

HCID 86646712HCID 86646712, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromo-thiophene-3-carboxylic acid (0.44 g, 2.18 mmol) was dissolved in acetonitrile (3 mL) and decahydroquinoline (a 3:2 mixture of cis- to trans-isomers; 2 mL) then HATU (2.18 mmol) was added. The reaction mixture was stirred overnight, and then the solvent evaporated and the residue purified by flash chromatography on silica eluting with 0-50% ethyl acetate in cyclohexane. The fractions containing the desired cis-product were concentrated under vacuum to give the title compound (0.63 g) as a colourless gum. LCMS m/z 330.36 [M+H]+ R.T.=4.09 min. (Analytical Method 5).

Workup

  1. customthe solvent evaporated
  2. customthe residue purified by flash chromatography on silica eluting with 0-50% ethyl acetate in cyclohexane
  3. additionThe fractions containing the desired cis-product
  4. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-7dc9540b0b9f4f70b3936e89ff25c904
Source dataset
uspto-grants-2013_12
Patent number
US08614209B2

Reaction notes

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