5-Chloro-2-propyl-[1,8]naphthyridine → HCID 24897973, compound

HRID 2358549Notes

Reaction equation

HRID 2358549 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.[NH2:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[S:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1>>[CH3:22][C:20]1[CH:19]=[CH:18][C:17]([S:23][C:24]2[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=2)=[C:16]([NH:15][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:21]=1

Participants

3

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenol

Product 1

HCID 24897973HCID 24897973, compound

Procedure

The product from Example 2g (275 mg, 0.133 mmol) was reacted with the product from Example 4c (231 mg, 0.133 mol) for 5 h following the procedure from Example 1g giving the title compound after purification of the crude product by HPLC with TFA as the trifluoroacetic acid salt (288 mg, 42%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 2H) 1.85 (m, 2H) 2.33 (s, 3H) 3.00 (t, J=7.35 Hz 2H) 6.29 (d, J=6.99 Hz, 1H) 6.73 (d, J=8.46 Hz, 2H) 7.00 (m, 2H) 7.19 (d, J=8.46 Hz, 2H) 7.27 (s, 1H) 7.83 (d, J=8.82 Hz, 1H) 8.43 (d, J=7.35 Hz, 1H) 9.04 (d, J=8.46 Hz, 1H) 9.90 (s, 1H) 11.04 (s, 1H) 14.40 (br. s, 1H); MS (ESI+) m/z 402 (M+H)+.

Sources & evidence

ORD record
ord-744b31dfcf884d30b9111542da53e45b
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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