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

HRID 2358719Notes

Reaction equation

HRID 2358719 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]=[CH:23][CH:22]=2)[CH:16]=[CH:15][C:14]=1[S:27][C:28]1[CH:33]=[CH:32][C:31]([OH:34])=[CH:30][CH:29]=1>>[CH2:20]([O:19][C:17]1[CH:16]=[CH:15][C:14]([S:27][C:28]2[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=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)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 124225244-Chloro-1,8-naphthyridineHCID 668085974-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenol

Product 1

HCID 684584034-[4-Benzyloxy-2-([1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 16c (100 mg, 0.559 mmol) was reacted with 4-(2-amino-4-benzyloxy-phenylsulfanyl)-phenol (224 mg, 0.559 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 (mg, %). 1H NMR (300 MHz, DMSO-d6) δ ppm: 5.14 (s, 2 H), 6.31 (d, J=6.99 Hz, 1 H), 6.61-6.69 (m, 2 H), 7.08-7.23 (m, 5 H), 7.32-7.46 (m, 5 H), 7.92 (dd, J=8.46, 4.41 Hz, 1 H), 8.47 (d, J=6.99 Hz, 1 H), 9.10-9.21 (m, 2 H), 9.77 (s, 1 H), 11.14 (s, 1 H); MS (ESI+) m/z 452 (M+H−TFA)+; (ESI−) m/z 450 (M−H−TFA)−.

Sources & evidence

ORD record
ord-fc950b9b4f674ac4b43721a77563a311
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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