Triethylamine → 6-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamide

HRID 2079961노트

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HRID 2079961 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH2:11]([C:18]1[S:22][C:21]([CH2:23][NH2:24])=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=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>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:24][CH2:23][C:21]2[S:22][C:18]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:19][CH:20]=2)=[O:8])=[CH:4][N:3]=1

참가 물질

9

반응물 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphateHCID 231306122-Thiophenemethanamine,5-(phenylmethyl)-

생성물 1

HCID 231303536-amino-N-(5-benzylthiophen-2-ylmethyl)-nicotinamide수율 29.5%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매4회

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온도
60 °C

실험 절차

To a solution of 6-aminonicotinic acid (340 mg, 2.4 mmol) and C-(5-benzyl-thiophen-2-yl)-methylamine described in Preparation Example 42 (450 mg, 2.2 mmol) in N,N-dimethylformamide (5 mL) were added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (1.1 g, 2.4 mmol) and triethylamine(0.62 mL, 4.4 mmol), and the solution was stirred at 60° C. for 1 hour. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed twice with water. Silica gel was added to the organic layer, the solvent was evaporated in vacuo adsorption, purification was carried out by NH silica gel column chromatography (hexane:ethyl acetate=1:1, then ethyl acetate, then ethyl acetate:methanol=10:1), and 6-amino-N-(5-benzyl-thiophen-2-ylmethyl)-nicotinamide (210 mg, 0.65 mmol, 29.5%) was obtained.

후처리

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

출처 및 근거

ORD 기록
ord-07255c3963894ecca90e46bbafeb493a
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07932272B2

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