5-Chloro-2-propyl-[1,8]naphthyridine → 4-[4-(3-Bromo-benzyloxy)-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

HRID 2358703Notes

Reaction equation

HRID 2358703 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH2:13][CH3:14])=[N:7]2.[NH2:15][C:16]1[CH:21]=[C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([Br:30])[CH:25]=2)[CH:19]=[CH:18][C:17]=1[S:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=1>>[Br:30][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][CH:27]=1)[CH2:23][O:22][C:20]1[CH:19]=[CH:18][C:17]([S:31][C:32]2[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=2)=[C:16]([NH:15][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:21]=1

Participants

3

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 668082684-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenol

Product 1

HCID 684582444-[4-(3-Bromo-benzyloxy)-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 2g (62 mg, 0.30 mmol) was reacted with 4-[2-Amino-4-(3-bromo-benzyloxy)-phenylsulfanyl]-phenol (120 mg, 0.30 mmol) for 48 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 (86 mg, 41%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.73 Hz, 3 H) 1.85 (dt, J=7.73 Hz, 2 H) 3.00 (dd, J=7.72 Hz, 2 H) 5.15 (s, 2 H) 6.27 (d, J=7.35 Hz, 1 H) 6.66 (d, J=8.82 Hz, 2 H) 7.07-7.69 (m, 7 H) 7.65 (s, 1 H) 7.83 (d, J=8.82 Hz, 1 H) 8.41 (d, J=6.99 Hz, 1 H) 9.03 (d, J=8.82 Hz, 1 H) 9.81 (s, 1 H) 11.05 (br s, 1 H) 14.43 (br s, 1 H); MS (ESI+) m/z 572, 574 (M+H−TFA)+; (ESI−) m/z 570-572 (M−H−TFA)−.

Sources & evidence

ORD record
ord-a084651fb91446668a24751d9853caf4
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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