5-Chloro-2-propyl-[1,8]naphthyridine → 3-[4-Methyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

HRID 2358655Notes

Reaction equation

HRID 2358655 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:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=1>>[CH3:22][C:20]1[CH:19]=[CH:18][C:17]([S:23][C:24]2[CH:25]=[C:26]([OH:30])[CH:27]=[CH:28][CH:29]=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 574699063-(2-Amino-4-methyl-phenylsulfanyl)-phenol

Product 1

HCID 684595843-[4-Methyl-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 2g (275 mg, 1.33 mmol) was reacted with the product from Example 52b (307 mg, 1.33 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 (305 mg, 45%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (t, J=7.35 Hz, 3 H) 1.75-1.94 (m, 2 H) 2.38 (s, 3 H) 2.98 (t, J=7.35 Hz, 2 H) 6.30 (d, J=6.99 Hz, 1 H) 6.49-6.66 (m, 3H) 6.91-7.04 (m, 1 H) 7.29-7.44 (m, 3 H) 7.79 (d, J=8.82 Hz, 1 H) 8.39 (d, J=7.35 Hz, 1 H) 8.96 (d, J=8.46 Hz, 1 H) 9.57 (s, 1 H) 10.95 (s, 1 H) 14.34 (s, 1 H); MS (ESI+) m/z 402 (M+H−TFA)+.

Sources & evidence

ORD record
ord-9a04b5327f02497fa06c066269bcb3fc
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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