Diisopropylethylamine → N-((R)-1-((S)-2-cyanopyrrolidine-1-yl)-1-oxopropan-2-yl)quinoline-4-carboxamide

HRID 528688Notes

Reaction equation

HRID 528688 reaction equation
Cl.[N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](Cl)=[O:13])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.CC1C=CC(S(O)(=O)=O)=CC=1.[NH2:35][C@H:36]([CH3:46])[C:37]([N:39]1[CH2:43][CH2:42][CH2:41][C@H:40]1[C:44]#[N:45])=[O:38]>C(Cl)Cl>[C:44]([C@@H:40]1[CH2:41][CH2:42][CH2:43][N:39]1[C:37](=[O:38])[C@H:36]([NH:35][C:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[N:2]=[CH:3][CH:4]=1)=[O:13])[CH3:46])#[N:45]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12373997Quinoline-4-carbonyl chloride hydrochlorideHCID 89705053(S)-1-((R)-2-aminopropanoyl)pyrrolidine-2-carbonitrile 4-methylbenzenesulfonate

Product 1

HCID 89705242N-((R)-1-((S)-2-cyanopyrrolidine-1-yl)-1-oxopropan-2-yl)quinoline-4-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Quinoline-4-carbonyl chloride hydrochloride (0.067 g, 0.295 mmol) was added to a mixture of DIPEA (0.160 ml, 0.913 mmol) and (S)-1-((R)-2-aminopropanoyl)pyrrolidine-2-carbonitrile 4-methylbenzenesulfonate (0.100 g, 0.295 mmol) in DCM. After 3 h the mixture was washed with 1N citric acid and saturated sodium bicarbonate and brine. The organic layer was dried sodium sulfate, filtered and purified by column chromatography using a mixture of ethylacetate and methanol as eluents.

Workup

  1. washAfter 3 h the mixture was washed with 1N citric acid and saturated sodium bicarbonate and brine
  2. filtrationfiltered
  3. custompurified by column chromatography
  4. additiona mixture of ethylacetate and methanol as eluents

Sources & evidence

ORD record
ord-98b31889b38046e9a4ab9e46f77680d4
Source dataset
uspto-grants-2016_05
Patent number
US09346814B2

Reaction notes

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