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

HRID 2068649ノート

反応式

HRID 2068649 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-3a0d084bd1664222afd75d962dfbe2ac
出典データセット
uspto-grants-2012_10
特許番号
US08299063B2

反応ノート

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