Triethylamine → [5-(6-Fluoro-pyridin-3-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

HRID 2068649Notes

Reaction equation

HRID 2068649 reaction equation
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=2)=[CH:4][CH:3]=1.[CH2:16]1[C@H:25]2[C@@H:20]([CH2:21][CH2:22][CH2:23][CH2:24]2)[CH2:19][CH2:18][NH:17]1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(#N)C>[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]=[C:10]([C:13]([N:17]3[CH:16]4[CH:25]([CH2:24][CH2:23][CH2:22][CH2:21]4)[CH2:20][CH2:19][CH2:18]3)=[O:15])[CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11083964trans-DecahydroisoquinolineHCID 581101925-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acid

Product 1

HCID 44226878[5-(6-Fluoro-pyridin-3-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanoneYield 19.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acid (0.05 g, 0.22 mmol) was dissolved in acetonitrile (1 mL) together with cis, trans-decahydroisoquinoline (0.134 mL, 0.90 mmol), triethylamine (80 μL, 0.60 mmol) and HATU (0.085 g, 0.22 mmol) and the resulting mixture was stirred over the weekend. The crude material was purified by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were evaporated to give the title compound as a pink oil (0.015 g). LCMS m/z 345.23 [M+H]+ R.T.=11.76 min (Analytical Method 2).

Workup

  1. customThe crude material was purified by HPLC
  2. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  3. additionThe fractions containing the desired product
  4. customwere evaporated

Sources & evidence

ORD record
ord-3a0d084bd1664222afd75d962dfbe2ac
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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