Triethylamine → HCID 86646698, compound

HRID 1809054Notes

Reaction equation

HRID 1809054 reaction equation
[F:1][C:2]([F:13])([F:12])[CH2:3][C:4]1[S:8][CH:7]=[C:6]([C:9]([OH:11])=O)[CH:5]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[NH:45]1[CH:54]2[CH:49]([CH2:50][CH2:51][CH2:52][CH2:53]2)[CH2:48][CH2:47][CH2:46]1>CN(C=O)C.O.C(#N)C>[N:45]1([C:9]([C:6]2[CH:5]=[C:4]([CH2:3][C:2]([F:1])([F:13])[F:12])[S:8][CH:7]=2)=[O:11])[C@@H:54]2[C@@H:49]([CH2:50][CH2:51][CH2:52][CH2:53]2)[CH2:48][CH2:47][CH2:46]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 92911DecahydroquinolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59542565HCID 59542565, compound

Product 1

HCID 86646698HCID 86646698, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

5-(2,2,2-Trifluoro-ethyl)-thiophene-3-carboxylic acid (0.05 g, 0.32 mol) was dissolved in DMF (2 mL). HATU (0.23 mmol), triethylamine (1.5 mmol) and decahydroquinoline (3:2 mixture of cis- and trans-isomers; 0.64 mmol) were added and the reaction stirred overnight. The reaction mixture was then diluted with water and acetonitrile and separated by HPLC, eluting with 10%-98% acetonitrile in water (0.1% formic acid). The fractions containing the desired product were concentrated under vacuum to give the title compound (21.2 mg). LCMS m/z 332.12 [M+H]+ RT=11.62 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 7.4 (s, 1H), 7.1 (s, 1H), 4.6 (m, 1H), 3.8-3.7 (m, 1H), 3.6 (q, 2H), 3.1-2.8 (m, 1H), 2.0-1.1 (m, 13H).

Workup

  1. customseparated by HPLC
  2. washeluting with 10%-98% acetonitrile in water (0.1% formic acid)
  3. additionThe fractions containing the desired product
  4. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-c5fe47734c7d41ef9a70b1c5417dce2c
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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