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

HRID 2197868Notes

Reaction equation

HRID 2197868 reaction equation
Cl[C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=2)[CH:16]=[CH:15][C:14]=1[S:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=1>>[Br:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[CH2:20][O:19][C:17]1[CH:16]=[CH:15][C:14]([S:28][C:29]2[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=2)=[C:13]([NH:12][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[CH:4][CH:3]=2)[CH:18]=1

Participants

3

Reactant 2

HCID 124225244-Chloro-1,8-naphthyridineHCID 668082684-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 684617784-[4-(3-Bromo-benzyloxy)-2-([1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 16c (50 mg, 0.30 mmol) was reacted with 4-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenol (120 mg, 0.30 mmol) for 40 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 (87 mg, 45%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 5.15 (s, 2H) 6.30 (d, J=6.99 Hz, 1H) 6.66 (d, J=8.83 Hz, 2H) 7.08-7.47 (m, 6H) 7.56 (d, J=7.72 Hz, 1H) 7.65 (m, 1H) 7.92 (dd, J=4.41 Hz, J=8.46 Hz, 1H) 8.18 (d, J=6.99 Hz, 1H) 9.14 (dd, J=8.83 Hz, 1H) 9.17 (dd, J=5.88 Hz, J=1.84 Hz, 1H) 9.80 (s, 1H) 11.16 (br s, 1H) 14.53 (br s, 1H); MS (ESI+) m/z 529, 531 (M+H−TFA)=; (ESI−) m/z 528, 530 (M−H−TFA)−.

Sources & evidence

ORD record
ord-42426303b5fa4263b021c4004fc33c29
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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