Triethylamine → [5-(2-Fluoro-pyridin-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

HRID 2068651Notes

Reaction equation

HRID 2068651 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]2[S:12][CH:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=2)[CH:5]=[CH:4][N: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[CH:7]=[C:6]([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:5]=[CH:4][N: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 581102975-(2-Fluoro-pyridin-4-yl)-thiophene-3-carboxylic acid

Product 1

HCID 44226876[5-(2-Fluoro-pyridin-4-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanoneYield 26.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-(2-Fluoro-pyridin-4-yl)-thiophene-3-carboxylic acid (0.05 g, 0.22 mmol) was dissolved in acetonitrile (2 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 an oil (0.02 g). LCMS m/z 345.22 [M+H]+ R.T.=11.64 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-4d5de77952834e8daa0a80ab703559e8
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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