2-Morpholinoethylamine → HCID 69320856, compound

HRID 2113582Notes

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

Participants

Reactant 2

HCID 4082852-Morpholinoethylamine

HCID 69184509HCID 69184509, compound

Product 1

HCID 69320856HCID 69320856, compoundYield 55%

Procedure

Following the procedure described above in Example 34, 6-fluoro-4-(1H-indol-5-ylamino)-1,7-naphthyridine-3-carbonitrile was reacted with 2-morpholin-4-yl-ethylamine. The crude product was purified by flash column chromatography (2 to 10% methanol in methylene chloride) to give a yellow solid (0.103 g, 55%). 1H NMR (400 MHz, DMSO-D6) δ ppm 2.4 (m, 4 H) 2.6 (t, J=6.8 Hz, 2 H) 3.4 (m, 2 H) 3.6 (m, 4 H) 6.5 (m, 2 H) 7.1 (dd, J=8.5, 1.9 Hz, 1 H) 7.2 (s, 1 H) 7.4 (m, 1 H) 7.4 (d, J=8.6 Hz, 1 H) 7.5 (d, J=1.8 Hz, 1 H) 8.1 (s, 1 H) 8.8 (s, 1 H) 9.7 (s, 1 H) 11.2 (s, 1 H).

Workup

customThe crude product was purified by flash column chromatography (2 to 10% methanol in methylene chloride)

Sources & evidence

ORD record: ord-8b6db88eb33943fb9bd6b75ec333ccf0
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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