4-(2-Amino-4-methyl-phenylsulfanyl)-phenol → 4-[2-(7-Ethyl-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenol

HRID 2197712Notes

Reaction equation

HRID 2197712 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:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.Cl[C:18]1[CH:27]=[CH:26][N:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH2:28][CH3:29])=[N:23]2>>[CH2:28]([C:22]1[N:23]=[C:24]2[C:19]([C:18]([NH:1][C:2]3[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=3[S:9][C:10]3[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=3)=[CH:27][CH:26]=[N:25]2)=[CH:20][CH:21]=1)[CH3:29]

Participants

3

Reactant 2

HCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 672512035-Chloro-2-ethyl-1,8-naphthyridine

Product 1

HCID 248977564-[2-(7-Ethyl-[1,8]naphthyridin-4-ylamino)-4-methyl-phenylsulfanyl]-phenol

Procedure

The product from Example 4c (131 mg, 0.530 mmol) was reacted with the product from Example 3f (97 mg, 0.503 mmol) for 21 h following the procedure from Example 1g giving the title compound as a hydrochloride salt which was triturated with 5:1 ether/THF giving (210 mg, 98%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 1.37 (t, J=7.35 Hz, 3H) 2.33 (s, 3H) 3.05 (q, J=7.35 Hz, 2H) 6.29 (d, J=6.99 Hz, 1H) 6.74 (d, J=8.46 Hz, 2H) 7.00 (m, 1H) 7.17-7.29 (m, 4H) 7.84 (d, J=8.83 Hz, 1H) 8.43 (d, J=6.98 Hz, 1H) 9.09 (d, J=8.83 Hz, 1H) 9.90 (s, 1H) 11.12 (br s, 1H) 14.38 (br s, 1H); MS (ESI+) m/z 388 (M−Cl)+; (ESI−) m/z 386 (M−HCl)−.

Sources & evidence

ORD record
ord-144c131dcaed47eaa91b144ad00ec109
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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