2-Morpholinoethylamine → HCID 44405460, compound

HRID 2113578Notes

Reaction equation

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

Participants

Reactant 2

HCID 4082852-Morpholinoethylamine

HCID 69316825HCID 69316825, compound

Product 1

HCID 44405460HCID 44405460, compoundYield 48%

Procedure

Following the procedure described above in Example 34, 4-[(3-chloro-4-fluorobenzyl)amino]-6-fluoro-1,7-naphthyridine-3-carbonitrile was reacted with 2-morpholin-4-yl-ethylamine. The crude product was purified by flash column chromatography (1% methanol in methylene chloride) to give a yellow solid (0.14 g, 48%). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.4 (m, 4 H) 2.6 (m, 2 H) 3.4 (m, 2 H) 3.6 (m, 4 H) 5.0 (d, J=7.1 Hz, 2 H) 6.5 (m, 1 H) 7.0 (s, 1 H) 7.3 (m, 1 H) 7.4 (m, 1 H) 7.5 (dd, J=6.9, 1.9 Hz, 1 H) 8.1 (s, 1 H) 8.5 (m, 1 H) 8.8 (s, 1 H).

Workup

customThe crude product was purified by flash column chromatography (1% methanol in methylene chloride)

Sources & evidence

ORD record: ord-edbdc9f7473c43fd827d9467beca875d
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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