5-Chloro-2-methyl-1,8-naphthyridine → 4-[4-(4-Chloro-benzyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

HRID 2358720Notes

Reaction equation

HRID 2358720 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][C:25]([Cl:28])=[CH:24][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>>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][O:20][C:18]2[CH:17]=[CH:16][C:15]([S:29][C:30]3[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=3)=[C:14]([NH:13][C:2]3[C:3]4[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:19]=2)=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 68461220HCID 68461220, compound

Product 1

HCID 684611784-[4-(4-Chloro-benzyloxy)-2-(7-methyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 1d (100 mg, 0.559 mmol) was reacted with the product from Example 143a (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: 2.77 (s, 3 H), 5.16 (s, 2 H), 6.26 (d, J=6.99 Hz, 1 H), 6.65 (d, J=8.46 Hz, 2 H), 7.09-7.24 (m, 5 H), 7.37-7.44 (m, 3 H), 7.51 (s, 1H), 7.81 (d, J=8.82 Hz, 1 H), 8.40 (d, J=6.99 Hz, 1 H), 8.99 (d, J=8.82 Hz, 1 H), 9.80 (s, 1 H), 11.04 (s, 1 H); MS (ESI+) m/z 500 (M+H−TFA)+; (ESI−) m/z 498 (M−H−TFA)−.

Sources & evidence

ORD record
ord-9ca1ded523444ab2b2db8bda5ba400b0
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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