Diisopropylethylamine → HCID 25015094, compound

HRID 2424836Notes

Reaction equation

HRID 2424836 reaction equation
[CH3:1][C:2]1([OH:7])[CH2:6][CH2:5][NH:4][CH2:3]1.O[C@H]1CCNC1.[OH:14][C:15]1([CH2:22][NH:23][C:24]([C:26]2[C:27]3[CH:28]=[CH:29][C:30](Cl)=[N:31][C:32]=3[CH:33]=[CH:34][C:35]=2[Cl:36])=[O:25])[CH2:20][CH2:19][CH2:18][CH:17]([CH3:21])[CH2:16]1.C(N(C(C)C)CC)(C)C>C(#N)C.C(N(CC)CC)C>[Cl:36][C:35]1[CH:34]=[CH:33][C:32]2[N:31]=[C:30]([N:4]3[CH2:5][CH2:6][C:2]([OH:7])([CH3:1])[CH2:3]3)[CH:29]=[CH:28][C:27]=2[C:26]=1[C:24]([NH:23][CH2:22][C@:15]1([OH:14])[CH2:20][CH2:19][CH2:18][C@H:17]([CH3:21])[CH2:16]1)=[O:25]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733874(3S)-pyrrolidin-3-olHCID 145784583-Methylpyrrolidin-3-olHCID 866233652,6-Dichloro-quinoline-5-carboxylic acid (1-hydroxy-3methyl-cyclohexylmethyl)-amide

Product 1

HCID 25015094HCID 25015094, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Procedure

The title compound was prepared by the method of Example 1, step e) by reacting 3-methylpyrrolidin-3-ol (0.42 g) (instead of (S)-3-hydroxypyrrolidine) with 2,6-dichloro-quinoline-5-carboxylic acid (1-hydroxy-3-methyl-cyclohexylmethyl)-amide (0.10 g) and triethylamine (0.38 ml) (instead of diisopropylethylamine) in acetonitrile (1 ml) to afford the title compound crude and as a 1:1 mixture of diastereomers. The reaction was concentrated in vacuo and the products isolated by flash column chromatography (SiO2, 4% methanol/dichloromethane as eluent) as a colourless solid (70 mg). The diastereomers were separated by supercritical fluid chromatography (SFC) on an OJ Daicel column using 25% ethanol/carbon dioxide as eluent to afford Isomer 1 as a colourless solid (18 mg).

Workup

  1. customThe title compound was prepared by the method of Example 1, step e)

Sources & evidence

ORD record
ord-1979178b9a6a497bb19122871944c81d
Source dataset
uspto-grants-2011_06
Patent number
US07964616B2

Reaction notes

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