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

HRID 2358708Notes

Reaction equation

HRID 2358708 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][C:25]([F:28])=[CH:24][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>>[F:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:18]2[CH:17]=[CH:16][C:15]([S:29][C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)=[C:14]([NH:13][C:2]3[C:3]4[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:19]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 668084244-[2-Amino-4-(4-fluoro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 684596884-[4-(4-Fluoro-benzyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 1d (53 mg, 0.30 mmol) was reacted with 4-[2-amino-4-(4-fluoro-benzyloxy)-phenylsulfanyl]-phenol (102 mg, 0.30 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 (115 mg, 64%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.76 (s, 3H) 5.11 (s, 2 H) 6.26 (d, J=6.99 Hz, 1 H) 6.65 (d, J=8.46 Hz, 2 H) 7.10 (d, J=8.82 Hz, 2 H) 7.15-7.27 (m, 4 H) 7.49 (m, J=5.88 Hz, 2 H) 7.81 (d, J=8.46 Hz, 1 H) 8.40 (d, J=6.98 Hz, 1 H) 8.98 (d, J=8.46 Hz, 1 H) 9.78 (s, 1 H) 11.03 (br s,1 H) 14.36 (br s, 1 H); MS (ESI+) m/z, 484 (M+H−TFA)+; (ESI−) m/z, 482 (M−H−TFA)−.

Sources & evidence

ORD record
ord-7c33574223c64ddda7fc66fdf2c7b659
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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