Diisopropylethylamine → Ethyl 1-[6chloro-2-(1H-imidazol-5-ylcarbonyl)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl]cyclobutanecarboxylate Hydrochloride

HRID 1700370Notes

Reaction equation

HRID 1700370 reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([C:16]3([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17]3)[NH:9][CH2:8][CH2:7][C:6]2=1.C([N:44]1[CH:48]=[C:47]([C:49](O)=[O:50])[N:46]=[CH:45]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C(N(C(C)C)CC)(C)C.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>>[ClH:2].[Cl:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH:10]([C:16]3([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:17][CH2:18][CH2:19]3)[N:9]([C:49]([C:47]3[NH:46][CH:45]=[N:44][CH:48]=3)=[O:50])[CH2:8][CH2:7][C:6]2=1

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 105701171-Trityl-1H-imidazole-4-carboxylic acidHCID 18317933Ethyl 1-(6-chloro-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl)cyclobutanecarboxylate Hydrochloride

Product 1

HCID 18317902Ethyl 1-[6chloro-2-(1H-imidazol-5-ylcarbonyl)-2,3,4,9-tetrahydro-1H-beta-carbolin-1-yl]cyclobutanecarboxylate Hydrochloride

Procedure

1.84 g of the compound of Example 1, 1.8 g of N-tritylimidazole-4-carboxylic acid, 1.92 ml of diisopropylethylamine and 1.76 g of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate are stirred at ambient temperature for 24 hours. After dilution with 500 ml of water, filtration, and extraction with dichloromethane, the organic phases are dried and filtered and then concentrated under reduced pressure. Crystallisation of the residue in an ethanol-diethyl ether-hydrogen chloride mixture enables the expected compound to be isolated.

Workup

  1. filtrationAfter dilution with 500 ml of water, filtration, and extraction with dichloromethane
  2. customthe organic phases are dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customCrystallisation of the residue in an ethanol-diethyl ether-hydrogen chloride mixture
  6. customto be isolated

Sources & evidence

ORD record
ord-62aca8613faf4ffb8e9f3309ef302de2
Source dataset
uspto-grants-2002_02
Patent number
US06350757B1

Reaction notes

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