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

반응식

HRID 468677 반응식
[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]

참가 물질

6

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f5d9f12ba6a748538b64152d7fd060bc
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08624040B2

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