2-Morpholinoethylamine → HCID 69317606, compound

HRID 2113581Notes

Reaction equation

F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([CH3:23])[CH3:22])=[CH:17][CH:16]=1.[N:24]1([CH2:30][CH2:31][NH2:32])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>>[CH:21]([C:18]1[CH:19]=[CH:20][C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][N:11]=[C:2]([NH:32][CH2:31][CH2:30][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])=[CH:16][CH:17]=1)([CH3:23])[CH3:22]

Participants

Reactant 2

HCID 4082852-Morpholinoethylamine

HCID 69183841HCID 69183841, compound

Product 1

HCID 69317606HCID 69317606, compoundYield 55%

Procedure

Following the procedure described above in Example 34, 6-fluoro-4-[(4-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile was reacted with 2-morpholin-4-yl-ethylamine. The crude product was purified by flash column chromatography (2% methanol in methylene chloride) to give a yellow solid (0.11 g, 55%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (d, J=6.8 Hz, 6 H) 2.4 (m, 4 H) 2.6 (m, 2 H) 2.9 (qt, 1 H) 3.3 (m, 1 H) 3.4 (m, 1 H) 3.6 (m, 4 H) 6.6 (m, 1 H) 7.0 (s, 1 H) 7.2 (d, J=8.6 Hz, 2 H) 7.3 (m, 2 H) 8.2 (s, 1 H) 8.8 (s, 1 H) 9.5 (s, 1 H).

Workup

customThe crude product was purified by flash column chromatography (2% methanol in methylene chloride)

Sources & evidence

ORD record: ord-f79c9875310045948dde1110b44b8c3a
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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