Triethylamine → Genz-10850

HRID 842029ノート

反応式

HRID 842029 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.Cl.[CH:15]1[C:27]2[CH:26]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:19]=2[CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C.CCN=C=NCCCN(C)C>ClCCl.CN(C1C=CN=CC=1)C>[CH:24]1[C:25]2[CH:26]([N:28]3[CH2:33][CH2:32][N:31]([C:10]([C:6]4[CH:5]=[C:4]5[C:9](=[CH:8][CH:7]=4)[NH:1][CH:2]=[CH:3]5)=[O:12])[CH2:30][CH2:29]3)[C:27]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20]=2[CH:21]=[CH:22][CH:23]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 742801H-Indole-5-Carboxylic AcidHCID 27461801-(9H-fluoren-9-yl)piperazine Dihydrochloride

生成物 1

HCID 447767Genz-10850

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Indole-5-carboxylic acid (17 mg, 0.11 mmole) and N-9-fluorenyl-piperazine dihydrochloride (32 mg, 0.1 mmole) were dissolved in 5 ml dichloromethane. To this solution was added triethylamine (2 eq. to neutralize HCl salt), catalytic DMAP and EDCI (33 mg, 0.11 mmole). The resulting mixture was stirred at room temperature overnight and was then worked up by washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride. The product was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH). 1H NMR (300 Mhz, CDCl3) δ 8.38 (s, 1H), 7.72-7.60 (m, 5H), 7.40-7.18 (m, 7H), 6.55 (d, 1H), 4.88 (s,1H), 3.60 (bs, 4H), 2.62 (bs, 4H).

後処理

  1. washby washing sequentially with 1N HCl, saturated sodium bicarbonate, and saturated sodium chloride
  2. customThe product was then purified by flash chromatography on silica gel (40:1 CHCl3/MeOH)

出典と根拠

ORDレコード
ord-ea8e4213f63649519ad707977dad32ba
出典データセット
uspto-grants-2002_04
特許番号
US06372752B1

反応ノート

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