2-Morpholinoethanol → HCID 69320628, compound

HRID 2113577Notes

Reaction equation

HRID 2113577 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[C:17](F)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[F:8].[OH:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[C:17]([O:23][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 611632-MorpholinoethanolHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 69320628HCID 69320628, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedure described above in Example 36, 4-(3-Chloro-4-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile was reacted with a 1 M solution of freshly prepared alkoxide of N-(2-hydroxyethyl)morpholine in THF. The product was collected by filtration to give a yellow solid (0.015 g, 8%). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.5 (m, 2 H) 2.7 (t, J=5.7 Hz, 2 H) 3.6 (m, 6 H) 4.3 (t, J=5.8 Hz, 2 H) 6.7 (ddd, J=8.7, 4.4, 2.5 Hz, 1 H) 6.8 (dd, J=6.8, 2.5 Hz, 1 H) 7.1 (dd, J=9.5, 8.7 Hz, 1 H) 7.4 (d, J=0.8 Hz, 1 H) 7.7 (s, 1 H) 8.4 (d, J=0.8 Hz, 1 H).

Workup

  1. filtrationThe product was collected by filtration

Sources & evidence

ORD record
ord-b35b689eadda4772a5780bfccbe661e9
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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