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

HRID 2079966
ノート
印刷プレビュー

反応式

HRID 2079966 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d8c10adf9e504f9795d7843c9ff6c635
出典データセット
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07932272B2

反応ノート

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