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

HRID 2358715Notes

Reaction equation

HRID 2358715 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]([Cl: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>>[Cl: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 684607244-[2-Amino-4-(3-chloro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 684609244-[4-(3-Chloro-benzyloxy)-2-([1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 16c (50 mg, 0.30 mmol) was reacted with the product from Example 144a (107 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 (109 mg, 60%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.77 (s, 3 H) 5.16 (s, 2 H) 6.25 (d, J=6.98 Hz, 1 H) 6.66 (d, J=8.83 Hz, 2 H) 7.07-7.25 (m, J=8.46 Hz, 5 H) 7.38-7.53 (m, 3 H) 7.80 (d, J=8.45 Hz, 1 H) 8.40 (d, J=6.99 Hz, 1 H) 8.99 (d, J=8.83 HZ, 1 H) 9.79 (s,1 H) 11.02 (br s,1H) 14.38 (br s,1 H); MS (ESI+) m/z 500 (M+H−TFA)+; (ESI−) m/z 498 (M−H−TFA)−.

Sources & evidence

ORD record
ord-1e72411af65b46c1a8d10e97961cd1f2
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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