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Triethylamine → 6-amino-N-(4-benzyloxy-benzyl)-nicotinamide

HRID 2079966
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HRID 2079966 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.[CH2:11]([O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=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.C(OCC)(=O)C.O>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:24][CH2:23][C:22]2[CH:25]=[CH:26][C:19]([O:18][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:20][CH:21]=2)=[O:8])=[CH:4][N:3]=1
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참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 184966-Aminonicotinic acidHCID 42928454-BenzyloxybenzylamineHCID 10938826Benzotriazol-1-yltris(dimethylamino)phosphonium hexafluorophosphate

생성물 1

HCID 231305886-amino-N-(4-benzyloxy-benzyl)-nicotinamide수율 64.4%

시약·촉매·용매 3

HCID 962
Water
용매
HCID 6228Dimethylformamide용매
HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of 6-aminonicotinic acid (130 mg, 0.941 mmol) and 4-benzyloxy-benzylamine (201 mg, 0.941 mmol) described in Preparation Example 1 in N,N-dimethylformamide (5 mL), was added benzotriazol-1-yl-tris(dimethylamino)phosphonium hexafluorophosphate (624 mg, 1.41 mmol) and triethylamine (394 μl, 2.82 mmol), and the solution was stirred for 40 minutes at 80° C. Water and ethyl acetate were added to the reaction solution, which was then partitioned, and the organic layer was washed twice with water. The solvent was evaporated in vacuo, ethyl acetate was added to the residue, a white insoluble matter was collected by filtration, and 6-amino-N-(4-benzyloxy-benzyl)-nicotinamide (202 mg, 0.606 mmol, 64%) was obtained.

후처리

  1. customwas then partitioned
  2. washthe organic layer was washed twice with water
  3. customThe solvent was evaporated in vacuo, ethyl acetate
  4. additionwas added to the residue
  5. filtrationa white insoluble matter was collected by filtration

출처 및 근거

ORD 기록
ord-d8c10adf9e504f9795d7843c9ff6c635
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932272B2

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