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

HRID 2197876Notes

Reaction equation

HRID 2197876 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][C:27]([Cl:30])=[CH:26][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>>[Cl:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][O:22][C:20]2[CH:19]=[CH:18][C:17]([S:31][C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)=[C:16]([NH:15][C:2]3[C:3]4[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=4)[N:9]=[CH:10][CH:11]=3)[CH:21]=2)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 441401765-Chloro-2-propyl-[1,8]naphthyridineHCID 68461220HCID 68461220, compound

Product 1

HCID 684592044-[4-(4-Chloro-benzyloxy)-2-(7-propyl-[1,8]naphthyridin-4-ylamino)-phenylsulfanyl]-phenol

Procedure

The product from Example 2g (85 mg, 0.41 mmol) was reacted with the product from Example 143a (146 mg, 0.41 mmol) for 26 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 (89 mg, 68%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 3H) 1.83 (sext, J=7.35 Hz, 2H) 3.00 (dd, J=7.35 Hz, 2H) 5.13 (s, 2H) 6.27 (d, J=6.99 Hz, 1H) 6.64 (d, J=8.82 Hz, 2H) 7.05-7.25 (m, J=8.45 Hz, 4H) 7.48 (m, 4H) 7.83 (d, J=8.45 Hz, 1H) 8.40 (d, J=6.99 Hz, 1H) 9.00 (d, J=8.46 Hz, 1H) 9.78 (s, 1H) 11.03 (br s, 1H) 14.40 (br s, 1H); MS (ESI+) m/z, 528, 530 (M+H−TFA)+; (ESI−) m/z, 526, 528 (M−H−TFA)−.

Sources & evidence

ORD record
ord-40db2e626334410ca697a94b4473a341
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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