5-Chloro-2-methyl-1,8-naphthyridine → HCID 68461218, compound

HRID 2358706Notes

Reaction equation

HRID 2358706 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]([F: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>>[F: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 668086774-[2-Amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 68461218HCID 68461218, compound

Procedure

The product from Example 1d (53 mg, 0.30 mmol) was reacted with 4-[2-amino-4-(3-fluoro-benzyloxy)-phenylsulfanyl]-phenol (102 mg, 0.30 mmol) for 20 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 (60 mg, 33%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.76 (s, 3H) 5.16 (s, 2 H) 6.27 (d, J=6.99 Hz, 1 H) 6.64 (d, J=8.46 Hz, 2 H) 7.03-7.36 (m, 7 H) 7.45 (m, J=6.26 Hz, 1 H) 7.80 (d, J=8.82 Hz, 1 H) 8.39 (d, J=6.98 Hz, 1 H) 8.99 (d, J=8.82 Hz, 1 H) 9.78 (s, 1 H) 11.02 (br s,1 H) 14.39 (br s,1 H); MS (ESI+) m/z,484 (M+H−TFA)+; (ESI−) m/z, 482 (M−H−TFA)−.

Sources & evidence

ORD record
ord-7b2bfba95f454984a782c3de2c7f58d2
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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