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

HRID 2358709Notes

Reaction equation

HRID 2358709 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][C:24]([F:27])=[CH:23][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>>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:17]2[CH:16]=[CH:15][C:14]([S:28][C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][CH:30]=3)=[C:13]([NH:12][C:2]3[C:11]4[C:6](=[N:7][CH:8]=[CH:9][CH:10]=4)[N:5]=[CH:4][CH:3]=3)[CH:18]=2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 124225244-Chloro-1,8-naphthyridineHCID 668084244-[2-Amino-4-(4-fluoro-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 684607644-[4-(4-Fluoro-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 4-[2-amino-4-(4-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 (99 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 5.11 (s, 2 H) 6.31 (d, J=6.99 Hz, 1 H) 6.64 (d, J=8.45 Hz, 2 H) 7.08-7.27 (m, 6 H) 7.50 (m, J=5.51 Hz, 2 H) 7.91 (d, J=4.41 Hz, 1 H) 8.47 (d, J=6.98 Hz, 1 H) 9.13 (dd, J=1.47 Hz, J=8.45 Hz, 1 H) 9.17 (dd, J=1.47 Hz, J=4.05 Hz, 1 H) 9.79 (s, 1 H) 11.14 (br s,1 H) 14.50 (br s,1 H); MS (ESI+) m/z,470 (M+H−TFA)+; (ESI−) m/z, 468 (M−H−TFA)−.

Sources & evidence

ORD record
ord-ff26680d5e914d808423896b01dd1cbf
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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