1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-(6-Bromonaphth-2-ylsulphonyl)-4-[4-(2-methyl-4-pyridyl)benzoyl]piperazine

HRID 586212

반응식

HRID 586212 반응식
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([S:28]([N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)(=[O:30])=[O:29])[CH:22]=[CH:21]2.Cl.CN(C)CCCN=C=NCC>CN(C=O)C>[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[CH:24]=[C:23]([S:28]([N:31]1[CH2:32][CH2:33][N:34]([C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([CH3:1])[CH:7]=4)=[CH:16][CH:15]=3)[CH2:35][CH2:36]1)(=[O:29])=[O:30])[CH:22]=[CH:21]2

참가 물질

5

반응물 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 186177484-(2-Methylpyridin-4-yl)benzoic acidHCID 223297091-(6-Bromonaphthalene-2-sulfonyl)piperazine

생성물 1

HCID 223297341-(6-Bromonaphth-2-ylsulphonyl)-4-[4-(2-methyl-4-pyridyl)benzoyl]piperazine수율 68%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-(2-Methyl-4-pyridyl)benzoic acid (62 mg), 1-(6-bromonaphth-2-ylsulphonyl) piperazine (94 mg) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (61 mg) were dissolved in DMF (2.5 ml) and the resultant solution stirred at ambient temperature for 16 hours. Excess DMF was removed in vacuo, water (10 ml) was added and the precipitate that formed was filtered, washed thoroughly with cold water and dried over P2O5. The solid thus obtained was purified by flash chromatography at 3 psi on silica (Merck ART 9385) eluting with 2.5% v/v methanol in dichloromethane. There was thus obtained the 1-(6-bromonaphth-2-ylsulphonyl)-4-[4-(2-methyl-4-pyridyl)benzoyl]piperazine (99 mg); mp 204-205° C.; 1H NMR (300 MHz, DMSO-d6) δ=2.48 (s,3H), 3.03 (s,4H), 3.57 (broad s, 4H), 7.46 (t,3H), 7.56 (s,1H), 7.77(d,2H), 7.83(d,2H), 8.17(q,2H), 8.42 (s,1H), 8.48 (d,2H) ppm; MS: m/z 550/552 (M+H)+ (1 Br pattern).

후처리

  1. customExcess DMF was removed in vacuo, water (10 ml)
  2. additionwas added
  3. customthe precipitate that formed
  4. filtrationwas filtered
  5. washwashed thoroughly with cold water
  6. dry with materialdried over P2O5
  7. customThe solid thus obtained
  8. customwas purified by flash chromatography at 3 psi on silica (Merck ART 9385)
  9. washeluting with 2.5% v/v methanol in dichloromethane

출처 및 근거

ORD 기록
ord-27674f96f7544a08b3e695d2ef22609d
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936610B2

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