Diisopropylethylamine → [5-(2-Methyl-2H-pyrazol-3-yl)-thiophen-3-yl]-octahydro-quinolin-1-yl-methanone

HRID 2068627Notes

Reaction equation

HRID 2068627 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[S:11][CH:10]=[C:9]([C:12]([OH:14])=O)[CH:8]=2)=[CH:5][CH:4]=[N:3]1.CCN(C(C)C)C(C)C.Cl.[NH:25]1[C@@H:34]2[C@@H:29]([CH2:30][CH2:31][CH2:32][CH2:33]2)[CH2:28][CH2:27][CH2:26]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1.O>[CH3:1][N:2]1[C:6]([C:7]2[S:11][CH:10]=[C:9]([C:12]([N:25]3[CH:34]4[CH:29]([CH2:30][CH2:31][CH2:32][CH2:33]4)[CH2:28][CH2:27][CH2:26]3)=[O:14])[CH:8]=2)=[CH:5][CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12229428cis-Decahydro-quinoline hydrochlorideHCID 581103265-(1-methyl-1H-pyrazol-5-yl)-3-thiophenecarboxylic acid

Product 1

HCID 44227723[5-(2-Methyl-2H-pyrazol-3-yl)-thiophen-3-yl]-octahydro-quinolin-1-yl-methanoneYield 76.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-(2-Methyl-2H-pyrazol-3-yl)-thiophene-3-carboxylic acid (0.084 g, 0.40 mmol) was dissolved in THF (2 mL) then DIPEA (0.22 mL, 1.3 mmol) and cis-decahydro-quinoline hydrochloride (DHQ [CIS-S]) (0.084 g, 0.48 mmol) were added followed by HATU (0.182 g, 0.48 mmol). The resulting mixture was stirred overnight then the mixture was diluted with water and extracted with DCM (×2). The organics were dried over sodium sulfate, filtered and evaporated. The crude material was purified by chromatography on a silica II cartridge, eluting with 50-100% ethyl acetate in cyclohexane. The fractions containing the desired product were concentrated under vacuum to give the title compound as a colourless oil (0.101 g). LCMS m/z 330.19 [M+H]+ R.T.=10.43 min (Analytical Method 2).

Workup

  1. extractionextracted with DCM (×2)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude material was purified by chromatography on a silica II cartridge
  6. washeluting with 50-100% ethyl acetate in cyclohexane
  7. additionThe fractions containing the desired product
  8. concentrationwere concentrated under vacuum

Sources & evidence

ORD record
ord-6177e9f8023b4b799bff23de909fee09
Source dataset
uspto-grants-2012_10
Patent number
US08299063B2

Reaction notes

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