Ethanol → HCID 68458469, compound

HRID 2358845Notes

Reaction equation

HRID 2358845 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[CH3:13][O:14][C:15](=[O:42])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:40])[CH3:39])=[CH:33][CH:32]=3)=[C:26]([NH2:41])[CH:25]=2)=[CH:18][CH:17]=1.[CH2:43](O)[CH3:44]>>[CH3:13][O:14][C:15](=[O:42])[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([S:30][C:31]3[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:40])[CH3:39])=[CH:33][CH:32]=3)=[C:26]([NH:41][C:2]3[C:3]4[C:8](=[N:7][C:6]([CH2:12][CH2:43][CH3:44])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:25]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68456665HCID 68456665, compound

Product 1

HCID 68458469HCID 68458469, compound

Procedure

The product from Example 1d (18 mg, 0.085 mmol) was reacted in ethanol (1 mL) with the product from Example 236a (35 mg, 0.085 mmol) for 18 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 (22 mg, 37%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3 H) 1.75-1.93 (m, 2 H), 2.02 (s, 3 H), 2.99 (t, J=7.54 Hz, 2 H), 3.86 (s, 3 H) 5.26 (s, 2 H) 6.30 (d, J=6.99 Hz, 1 H) 7.14 (d, J=8.82 Hz, 2 H), 7.17-7.27 (m, 2 H), 7.37 (d, J=8.46 Hz, 1 H), 7.42 (d, J=8.82 Hz, 2 H), 7.59 (d, J=8.46 Hz, 2 H), 7.80 (d, J=8.46 Hz, 1 H) 7.99 (d, J=8.09 Hz, 2 H), 8.36 (d, J=7.35 Hz, 1 H), 8.97 (d, J=8.46 Hz, 1 H) 9.98 (s, 1 H), 11.01 (s, 1 H), 14.38 (s, 1 H); MS (ESI+) m/z 593(M+H)+.

Sources & evidence

ORD record
ord-426aa4b9c7c84a6eaddd9cb91f9e621c
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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