Stannous chloride dihydrate → 7-(3,5-dimethyl-4-isoxazolyl)-6-(methoxy)-N4-(2-pyridinylmethyl)-3,4-quinolinediamine

HRID 1042988Notes

Reaction equation

[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[C:12]([N+:17]([O-])=O)[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:28][CH3:29])=[C:5]([CH3:30])[O:4][N:3]=1.O.O.Cl[Sn]Cl>C(O)C.Cl>[CH3:1][C:2]1[C:6]([C:7]2[CH:16]=[C:15]3[C:10]([C:11]([NH:20][CH2:21][C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][N:23]=4)=[C:12]([NH2:17])[CH:13]=[N:14]3)=[CH:9][C:8]=2[O:28][CH3:29])=[C:5]([CH3:30])[O:4][N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of this nitro intermediate (2.5 g, 24.82 mmol) in a mixture of ethanol (20 ml) and HCl (3.8 ml), was added portionwise SnCl2.2H2O (5.6 g, 24.82 mmol). The reaction mixture was heated to 40° C. for 1 h, then hydrolysed with sodium hydroxide N and extracted with DCM. The organic phase was washed with water, dried and concentrated to give the title compound as a brown powder (0.5 g, 17.8%). (APCI-MS) m/z: 376 MH+, Rt 2.46 min. 1H NMR (300 MHz, DMSO-d6, ppm) δ: 8.56 (d, 1H), 8.29 (s, 1H), 7.77 (dd, J=7.8, 7.6 Hz, 1H), 7.54 (s, 1H), 7.53-7.51 (m, 1H), 7.31-7.25 (m, 1H), 5.31 (s, 2H), 4.46 (d, J=7.2 Hz, 2H), 3.78 (s, 3H), 2.28 (s, 3H), 2.09 (s, 3H).

Workup

extractionhydrolysed with sodium hydroxide N and extracted with DCM
washThe organic phase was washed with water
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-297ba0dcb432406ab5f1a59da01a09a8
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08557984B2

Reaction notes

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