2-Morpholinoethylamine → HCID 44405504, compound

HRID 2113579Notes

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]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1.[N:28]1([CH2:34][CH2:35][NH2:36])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>>[N:28]1([CH2:34][CH2:35][NH:36][C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][N:11]=2)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]3[NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

Reactant 2

HCID 4082852-Morpholinoethylamine

HCID 185489566-Fluoro-4-(4-phenoxyanilino)-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 44405504HCID 44405504, compoundYield 44%

Procedure

Following the procedure described above in Example 34, 6-Fluoro-4-(4-phenoxy-phenylamino)-[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 (0.12 g, 44%). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.5 (m, 4 H) 2.6 (t, J=6.8 Hz, 2 H) 3.4 (m, 2 H) 3.6 (m, 4 H) 6.6 (t, J=5.6 Hz, 1 H) 7.0 (m, 2 H) 7.1 (m, 4 H) 7.4 (m, 3 H) 8.2 (s, 1 H) 8.3 (s, 1 H) 8.8 (s, 1 H) 9.6 (s, 1 H).

Workup

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

Sources & evidence

ORD record: ord-31bbaf2cb4674378be47173d88db7a3e
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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