Ethanol → HCID 68458795, compound

HRID 2358667Notes

Reaction equation

HRID 2358667 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH2:13][CH3:14])=[N:7]2.C(O)C.[NH2:18][C:19]1[CH:24]=[C:23]([CH3:25])[CH:22]=[CH:21][C:20]=1[S:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=1>>[CH3:25][C:23]1[CH:22]=[CH:21][C:20]([S:26][C:27]2[CH:32]=[CH:31][C:30]([CH2:33][OH:34])=[CH:29][CH:28]=2)=[C:19]([NH:18][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:24]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 68461166HCID 68461166, compound

Product 1

HCID 68458795HCID 68458795, compound

Procedure

The product from Example 2g as a 3.15M solution in ethanol (0.08 mL, 0.25 mmol) was reacted with the product from Example 115b (0.061 g, 0.25 mmol) for 18.5 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 (0.0195 g, 14%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 3 H) 1.75-1.93 (m, 2 H) 2.31-2.42 (s, 3 H) 2.91-3.08 (m, 2 H) 4.42 (s, 2 H) 6.30 (d, J=6.99 Hz, 1 H) 7.11-7.42 (m, 7 H) 7.81 (d, J=8.46 Hz, 1 H) 8.39 (d, J=6.99 Hz, 1 H) 8.98 (d, J=8.82 Hz, 1 H) 11.01 (s, 1 H); MS (ESI+) m/z 416.2 (M+H)+, (ESI−) m/z 414.3 (M−H)−.

Sources & evidence

ORD record
ord-76e30375d2924a0282242564bf2bdd00
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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