Diisopropylethylamine → HCID 57559117, compound

HRID 1723799Notes

Reaction equation

HRID 1723799 reaction equation
[CH3:1][C:2]1([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH2:5][CH2:4][NH:3]1.[F:21][C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[F:31])[C:25](Cl)=[O:26].CCN(C(C)C)C(C)C>C(Cl)(Cl)Cl>[F:21][C:22]1[CH:23]=[C:24]([C:25]([N:3]2[CH2:4][CH2:5][C:6]3[C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[NH:13][C:14]=3[C:2]2([CH3:1])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:26])[CH:28]=[CH:29][C:30]=1[F:31]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27245193,4-Difluorobenzoyl chlorideHCID 10491737HCID 10491737, compound

Product 1

HCID 57559117HCID 57559117, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was prepared by the addition of 1-methyl-1-phenyl-1,3,4,9-tetrahydrobeta-carboline (105 mg, 400 μmol), CHCl3 (9 mL), 3,4-difluorobenzoyl chloride (85 mg, 480 μmol), and DIEA (140 μL, 800 μmol) to a 25 mL flask. The solution was allowed to stir at 60° C. under N2 for 17 hours. The reaction solution was concentrated, and the crude sample was chromatographed (SiO2, 100% hexane to 20% EtOAc) to yield 35 mg of title compound; 1H NMR (CDCl3) δ 7.54 (1H, d), 7.48 (2H, d), 7.12-7.32 (9H, m), 4.05 (1H, m), 3.64-3.70 (1H, m), 3.19 (1H, m), 2.96 (1H, m), 2.29 (3H, s); MS (ESI): 403 (MH+).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe crude sample was chromatographed (SiO2, 100% hexane to 20% EtOAc)

Sources & evidence

ORD record
ord-79f40e226bc24467a106e39792ac9e7e
Source dataset
uspto-grants-2009_02
Patent number
US07485634B2

Reaction notes

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