Diisopropylethylamine → HCID 46901485, compound

HRID 1019695Notes

Reaction equation

[OH:1][CH2:2][C:3]1[O:7][N:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]=1.C(N(CC)C(C)C)(C)C.Cl[C:23](OC1C=CC([N+]([O-])=O)=CC=1)=[O:24].[Cl:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]=[C:41]([N:46]1[CH2:51][CH2:50][CH:49]([CH2:52][CH2:53][NH2:54])[CH2:48][CH2:47]1)[CH:40]=[CH:39]2>ClCCl.ClCCCl>[Cl:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][CH:45]=1)[N:42]=[C:41]([N:46]1[CH2:47][CH2:48][CH:49]([CH2:52][CH2:53][NH:54][C:23]([O:1][CH2:2][C:3]3[O:7][N:6]=[C:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH:4]=3)=[O:24])[CH2:50][CH2:51]1)[CH:40]=[CH:39]2

Participants

Conditions

Temperature: 10 °C

Procedure

To a solution of 3.54 g (20.70 mmol) of ethyl 5-hydroxymethylisoxazole-3-carboxylate (commercial), 7.88 mL (41.41 mmol) of N,N-diisopropylethylamine and 1.26 g (10.35 mmol) of N,N-dimethylaminopyridine in 120 mL of dichloromethane, cooled to 0° C., are added portionwise 4.17 g (20.70 mmol) of p-nitrophenyl chloroformate. The mixture is stirred at 10° C. for 2 hours and then evaporated to dryness. The residue obtained is taken up in 120 mL of 1,2-dichloroethane, followed by addition of 6.00 g (20.70 mmol) of 2-[1-(6-chloroquinolin-2-yl)piperidin-4-yl]ethylamine, obtained in step 11.2. and 5 mL (26.27 mmol) of N,N-diisopropylethylamine. The mixture is heated at 70° C. for 12 hours.

Workup

customevaporated to dryness
customThe residue obtained
customobtained in step 11.2
temperatureThe mixture is heated at 70° C. for 12 hours

Sources & evidence

ORD record: ord-524914dc7cb34a1ab3cf5dde5a8f5483
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716289B2

Reaction notes

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