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Triethylamine → Thieno[2,3-b]pyridine-5-carboxylic acid (5-phenoxy-thiophen-2-ylmethyl)-amide

HRID 2080258
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HRID 2080258 반응식
[Li].[S:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([OH:13])=O)[CH:10]=[C:5]2[CH:4]=[CH:3]1.[O:14]([C:21]1[S:25][C:24]([CH2:26][NH2:27])=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.F[P-](F)(F)(F)(F)F.N1([P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C.O>[O:14]([C:21]1[S:25][C:24]([CH2:26][NH:27][C:11]([C:9]2[CH:10]=[C:5]3[CH:4]=[CH:3][S:2][C:6]3=[N:7][CH:8]=2)=[O:13])=[CH:23][CH:22]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 5

HCID 8471TriethylamineHCID 3028194LithiumHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 14025921Thieno[2,3-b]pyridine-5-carboxylic acidHCID 23130515C-(5-Phenoxy thiophen-2-yl)methylamine

생성물 1

HCID 58388082
Thieno[2,3-b]pyridine-5-carboxylic acid (5-phenoxy-thiophen-2-ylmethyl)-amide
수율 40%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Then, the lithium salt of the resulting thieno[2,3-b]pyridine-5-carboxylic acid, C-(5-phenoxy-thiophen-2-yl)-methylamine described in Preparation Example 26 (4.7 mg, 23 μmol), benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (14 mg, 32 μmol) and triethylamine (9 μl, 63 μmol) were dissolved in N,N-dimethylformamide (0.5 mL), and the solution was stirred at room temperature for 2 hours. Water and ethyl acetate were added to the reaction solution, the organic layer was partitioned, and washed with brine. The solvent was evaporated in vacuo, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), and the title compound (3.0 mg, 8.2 μmol, 40%) was obtained as a white solid.

후처리

  1. customthe organic layer was partitioned
  2. washwashed with brine
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

출처 및 근거

ORD 기록
ord-fe34dbaf75b6427caf637a2964197771
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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