Triethylamine → Genz-10850

HRID 842029Notes

Reaction equation

HRID 842029 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

HCID 447767Genz-10850

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ea8e4213f63649519ad707977dad32ba
Source dataset
uspto-grants-2002_04
Patent number
US06372752B1

Reaction notes

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