Ethanol → HCID 68460914, compound

HRID 2358665Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][CH3:17])=[O:15])=[CH:12][CH:11]=1.Cl[C:21]1[CH:30]=[CH:29][N:28]=[C:27]2[C:22]=1[CH:23]=[CH:24][C:25]([CH2:31][CH2:32][CH3:33])=[N:26]2.C(O)C>>[CH3:17][NH:16][C:14](=[O:15])[C:13]1[CH:18]=[CH:19][C:10]([S:9][C:3]2[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=2[NH:1][C:21]2[C:22]3[C:27](=[N:26][C:25]([CH2:31][CH2:32][CH3:33])=[CH:24][CH:23]=3)[N:28]=[CH:29][CH:30]=2)=[CH:11][CH:12]=1

Participants

Reactant 3

HCID 702Ethanol

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridine

HCID 68460819HCID 68460819, compound

Product 1

HCID 68460914HCID 68460914, compound

Procedure

The product from Example 85b (0.155 g, 0.57 mmol) was reacted with the product from Example 2g as a 3.15M solution in ethanol (0.18 mL, 0.57 mmol) for 24 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid salt (0.180 g, 56%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3 H) 1.72-1.91 (m, 2 H) 2.41 (s, 3 H) 2.75 (d, J=4.41 Hz, 3 H) 2.97 (t, J=7.35 Hz, 2 H) 6.36 (d, J=6.99 Hz, 1 H) 7.20 (d, J=8.46 Hz, 2 H) 7.33-7.47 (m, 2 H) 7.50 (d, 1 H) 7.63 (d, J=8.46 Hz, 2 H) 7.77 (d, J=8.82 Hz, 1 H) 8.30-8.44 (m, J=6.62, 6.62 Hz, 2 H) 8.91 (d, J=8.82 Hz, 1 H) 10.86-11.09 (s, 1 H); MS (ESI+) m/z 443.2 (M+H)+; (ESI−) m/z 441.2 (M−H)−.

Sources & evidence

ORD record: ord-17c7fadf35164bd59868cc0aaf410b19
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763731B2

Reaction notes

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