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Pyridine → 3-Benzyl-10-methoxy-1,2,3,4,4a,5-hexahydrobenzo[b]pyrazino[1,2-d][1,4]diazepin-6(7h)-one

HRID 80495
ノート
印刷プレビュー

反応式

HRID 80495 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14]N(CC2C=CC=CC=2)[CH2:12][CH:11]1[CH2:23][C:24]([OH:26])=O.[N:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.Cl.CN(C)[CH2:36][CH2:37]CN=C=NCC>CN(C)C=O>[CH2:32]([N:27]1[CH2:14][CH2:15][N:10]2[C:3]3[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=3[NH:1][C:24](=[O:26])[CH2:23][CH:11]2[CH2:12]1)[C:31]1[CH:37]=[CH:36][CH:28]=[CH:29][CH:30]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 1049PyridineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 667697652-(1-(2-Amino-5-methoxyphenyl)-4-benzylpiperazin-2-yl)acetic acid

生成物 1

HCID 667698133-Benzyl-10-methoxy-1,2,3,4,4a,5-hexahydrobenzo[b]pyrazino[1,2-d][1,4]diazepin-6(7h)-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of Example 12E (0.390 g, 1.097 mmol) in N,N-dimethylformamide (3.66 mL) were added pyridine (4.44 mL, 54.9 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.421 g, 2.195 mmol) and the mixture was stirred at room temperature for 1 hour. The solution was concentrated, water was added to the residue, and the product was extracted twice with ethyl acetate. The combined organic washes were dried over sodium sulfate, concentrated and dried under vacuum at room temperature overnight. It was then passed through a 5 gram silica gel cartridge eluting first with dichloromethane, then with 2% methanol/dichloromethane and finally with 5% methanol/dichloromethane to obtain the title compound. An aliquot of material was further purified for analytical purposes by preparative HPLC to afford the title compound as the trifluoroacetic acid salt. 1H NMR (500 MHz, DMSO-d6) δ ppm 10.21 (s, 1H), 9.52 (s, 1H), 7.54-7.48 (m, 5H), 6.90 (d, J=8.6, 1H), 6.70-6.60 (m, 2H), 4.45 (s, 2H), 3.74 (s, 3H), 3.67-3.07 (m, 7H), 3.22-3.04 (m, 2H), 2.61 (dd, J=7.0, 13.5, 1H), 2.00 (d, J=13.5, 1H); MS (ESI) m/z 338.1 (M+H)+.

後処理

  1. concentrationThe solution was concentrated
  2. additionwater was added to the residue
  3. extractionthe product was extracted twice with ethyl acetate
  4. dry with materialThe combined organic washes were dried over sodium sulfate
  5. concentrationconcentrated
  6. customdried under vacuum at room temperature overnight
  7. washeluting first with dichloromethane

出典と根拠

ORDレコード
ord-655a3e0a02bc4f9fa2fccaae604369b1
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08846663B2

反応ノート

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