2-Morpholinoethylamine → HCID 44405465, compound

HRID 2113580Notes

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]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1.[N:25]1([CH2:31][CH2:32][NH2:33])[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1>>[N:25]1([CH2:31][CH2:32][NH:33][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]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=2)[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1

Participants

Reactant 2

HCID 4082852-Morpholinoethylamine

HCID 69321462HCID 69321462, compound

Product 1

HCID 44405465HCID 44405465, compoundYield 55%

Procedure

Following the procedure described above in Example 34, 6-fluoro-4-{[4-(trifluoromethyl)phenyl]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 (0.14 g, 55%). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.4 (m, 4 H) 3.4 (m, 2 H) 3.4 (m, 2 H) 3.6 (m, 4 H) 6.8 (m, 1 H) 6.9 (s, 1 H) 7.4 (d, J=8.3 Hz, 2 H) 7.7 (d, J=8.6 Hz, 2 H) 8.4 (s, 1 H) 8.9 (s, 1 H) 9.8 (s, 1 H).

Workup

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

Sources & evidence

ORD record: ord-93e801d5895048c59a08c388a75ba03b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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