Triethylamine → [5-(6-Fluoro-pyridin-3-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone

HRID 2068649노트

반응식

HRID 2068649 반응식
[F:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]=[C:10]([C:13]([OH:15])=O)[CH:9]=2)=[CH:4][CH: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[N:7]=[CH:6][C:5]([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:4][CH:3]=1

참가 물질

6

반응물 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 581101925-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acid

생성물 1

HCID 44226878[5-(6-Fluoro-pyridin-3-yl)-thiophen-3-yl]-(octahydro-quinolin-1-yl)-methanone수율 19.8%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

5-(6-Fluoro-pyridin-3-yl)-thiophene-3-carboxylic acid (0.05 g, 0.22 mmol) was dissolved in acetonitrile (1 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 a pink oil (0.015 g). LCMS m/z 345.23 [M+H]+ R.T.=11.76 min (Analytical Method 2).

후처리

  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

출처 및 근거

ORD 기록
ord-3a0d084bd1664222afd75d962dfbe2ac
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299063B2

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