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3-Methoxypropanoyl chloride → N-[2-((R)-Indan-1-ylamino)-quinolin-5-yl]-3-methoxy-propionamide

HRID 1671554
Notes
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Reaction equation

HRID 1671554 reaction equation
[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:17]([NH2:21])=[CH:16][CH:15]=[CH:14][C:13]=3[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:22][O:23][CH2:24][CH2:25][C:26](Cl)=[O:27]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C@H:1]1([NH:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][C:17]=3[NH:21][C:26](=[O:27])[CH2:25][CH2:24][O:23][CH3:22])[N:12]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 27597283-Methoxypropanoyl chlorideHCID 44219082(R)-N2-Indan-1-yl-quinoline-2,5-diamine

Product 1

HCID 44219235N-[2-((R)-Indan-1-ylamino)-quinolin-5-yl]-3-methoxy-propionamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

(R)—N2-Indan-1-yl-quinoline-2,5-diamine (150 mg, 0.55 mmol) was dissolved in 3 mL pyridine and 3-methoxypropionyl chloride (70 mg, 0.0.57 mmol) and 4-dimethylamino pyridine (3 mg, 0.02 mmol) were added. The reaction mixture was stirred at 80° C. overnight and quenched by addition of 50 mL water and acetic acid until pH 5. The mixture was extracted three times with ethyl acetate (50 mL each). The organic phases ware pooled, dried with sodium sulfate, filtered and evaporated. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0→0:100 gradient). The title compound was obtained as a brown solid (59 mg, 30%), MS: m/e=362.4 (M+H−).

Workup

  1. customquenched by addition of 50 mL water and acetic acid until pH 5
  2. extractionThe mixture was extracted three times with ethyl acetate (50 mL each)
  3. dry with materialdried with sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 100:0→0:100 gradient)

Sources & evidence

ORD record
ord-568569a246f84bb69173ca67056c6bb0
Source dataset
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07994324B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes