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

HRID 2197881Notes

Reaction equation

HRID 2197881 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.[NH2:13][C:14]1[CH:19]=[C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[CH:17]=[CH:16][C:15]=1[S:29][C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=1>>[Cl:28][C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[CH2:21][O:20][C:18]1[CH:17]=[CH:16][C:15]([S:29][C:30]2[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=2)=[C:14]([NH:13][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 684607244-[2-Amino-4-(3-chloro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 684593174-[4-(3-Chloro-benzyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 1d (71 mg, 0.40 mmol) was reacted with the product from Example 144a (143 mg, 0.41 mmol) for 24 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 (122 mg, 49%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.77 (s, 3H) 5.16 (s, 2H) 6.25 (d, J=6.98 Hz, 1H) 6.66 (d, J=8.83 Hz, 2H) 7.07-7.25 (m, J=8.46 Hz, 5H) 7.38-7.53 (m, 3H) 7.80 (d, J=8.45 Hz, 1H) 8.40 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.83 HZ, 1H) 9.79 (s, 1H) 11.02 (br s, 1H) 14.38 (br s, 1H); MS (ESI+) m/z 500 (M+H−TFA)+; (ESI−) m/z 498 (M−H−TFA)−.

Sources & evidence

ORD record
ord-e2fab796a7994364a1d6c173677396c8
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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