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Triethylamine → 6-Amino-N-(5-phenoxy thiophen-2-ylmethyl)-nicotinamide

HRID 2080213
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인쇄 미리보기

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HRID 2080213 반응식
[O:1]([C:8]1[S:12][C:11]([CH2:13][NH2:14])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=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.CO.C(OCC)(=O)C.O>[NH2:15][C:16]1[CH:24]=[CH:23][C:19]([C:20]([NH:14][CH2:13][C:11]2[S:12][C:8]([O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:9][CH:10]=2)=[O:21])=[CH:18][N:17]=1
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참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 23130515C-(5-Phenoxy thiophen-2-yl)methylamine

생성물 1

HCID 231305396-Amino-N-(5-phenoxy thiophen-2-ylmethyl)-nicotinamide수율 48.2%

시약·촉매·용매 4

HCID 887
Methanol
용매
HCID 962Water용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매2회

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온도
60 °C

실험 절차

To a solution of C-(5-phenoxythiophen-2-yl)methylamine described in Preparation Example 24 (170 mg, 0.83 mmol) and 6-aminonicotinic acid (130 mg, 0.91 mmol) in N,N-dimethylformamide (10 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (400 mg, 0.91 mmol) and triethylamine (0.3 mL, 2.2 mmol), and the solution was stirred for 35 minutes at 60° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, the organic layer was washed with water twice, NH silica gel was added to the organic layer, the solvent was evaporated in vacuo for adsorption, purification was carried out by NH silica gel column chromatography (ethyl acetate, then ethyl acetate:methanol=50:1), and the title compound (130 mg, 0.40 mmol, 48.2%) was obtained as a solid.

후처리

  1. customwas then partitioned
  2. washthe organic layer was washed with water twice
  3. additionNH silica gel was added to the organic layer
  4. customthe solvent was evaporated in vacuo for adsorption, purification

출처 및 근거

ORD 기록
ord-7593b1868c8d43b9a0e09fabd4404900
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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