Diisopropylethylamine → Ethyl 5-(3-chlorobenzo[b]thiophene-2-carbonyl)-7,7-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

HRID 468677

Reaction equation

HRID 468677 reaction equation
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([OH:13])=O.F[P-](F)(F)(F)(F)F.C[N+](C)=C(N(C)C)[O:24]N1C2N=CC=CC=2N=N1.C(N([CH2:45][CH3:46])C(C)C)(C)C.[CH3:47][C:48]1([CH3:67])[CH2:53][NH:52][CH2:51][C:50]2[CH:54]=[C:55]([C:57](NOC3CCCCO3)=[O:58])[S:56][C:49]1=2>CN(C)C=O>[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:11]([N:52]1[CH2:53][C:48]([CH3:47])([CH3:67])[C:49]2[S:56][C:55]([C:57]([O:58][CH2:45][CH3:46])=[O:24])=[CH:54][C:50]=2[CH2:51]1)=[O:13]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 3079643-Chloro-1-benzothiophene-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58157681HCID 58157681, compound

Product 1

HCID 66931717Ethyl 5-(3-chlorobenzo[b]thiophene-2-carbonyl)-7,7-dimethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-chloro-1-benzothiophene-2-carboxylic acid (23.4 mg, 0.11 mmol), N,N,N′,N′-tetramethyl-O-(7-azabenzotriazol-1-yl)uronium hexafluorophosphate (0.048 g, 0.11 mmol) and N,N-diisopropylethylamine (52.2 μL, 0.3 mmol) in N,N-dimethylformamide (1 mL, 12.9 mmol) was stirred at room temperature for 15 minutes. A solution of 7,7-dimethyl-N-(tetrahydro-2H-pyran-2-yloxy)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxamide (31 mg, 0.1 mmol) in N,N-dimethylformamide (1 mL) was then added and the reaction was further stirred at room temperature overnight. The solution was evaporated to dryness and the residue obtained was partitioned between DCM (2 mL) and half-saturated aqueous sodium bicarbonate solution (2 mL). Upon separation of the layers, the aqueous layer was extracted with additional DCM (2 mL) and the combined organic layers were concentrated to dryness to afford the title compound.

Workup

  1. customThe solution was evaporated to dryness
  2. customthe residue obtained
  3. customwas partitioned between DCM (2 mL) and half-saturated aqueous sodium bicarbonate solution (2 mL)
  4. customUpon separation of the layers
  5. extractionthe aqueous layer was extracted with additional DCM (2 mL)
  6. concentrationthe combined organic layers were concentrated to dryness

Sources & evidence

ORD record
ord-f5d9f12ba6a748538b64152d7fd060bc
Source dataset
uspto-grants-2014_01
Patent number
US08624040B2

Linked notes

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