Dimethylamine → N-{4-[4-(Benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}-3,4-bis(dimethylamino)butanamide

HRID 2416087Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:33][CH2:34][CH3:35])=[C:21]([NH:24][C:25](=[O:32])/[CH:26]=[CH:27]/[CH2:28][N:29]([CH3:31])[CH3:30])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:36]#[N:37])=[CH:11][C:10]=1[Cl:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:41][NH:42][CH3:43]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:39]=[CH:38][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:33][CH2:34][CH3:35])=[C:21]([NH:24][C:25](=[O:32])[CH2:26][CH:27]([N:42]([CH3:43])[CH3:41])[CH2:28][N:29]([CH3:31])[CH3:30])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:36]#[N:37])=[CH:11][C:10]=1[Cl:40])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 36 °C

Procedure

A solution of (E)-N-{4-[4-(benzyloxy)-3-chloroanilino]-3-cyano-7-ethoxy-6-quinolinyl}-4-(dimethylamino)-2-butenamide (400 mg, 0.719 mmol) and 1.5 mL of 2N dimethylamine in THF was heated at 36° C. in a sealed tube for 20 hours. After the volatile solvents were stripped off, the residue was treated with 1.5 mL of 2N dimethylamine in THF, and heated again at 36° C. in a sealed tube for 20 hours. After the solvent was removed, the residue was purified by preparatory TLC (developed in ethyl acetate:methanol:triethylamine=10:1:1) to yield 260 mg of the title compound as a yellow solid (yield: 60%), mp 102-104° C.; MS (ES) 601.3 (M+1).

Workup

customAfter the solvent was removed
customthe residue was purified by preparatory TLC (developed in ethyl acetate:methanol:triethylamine=10:1:1)

Sources & evidence

ORD record: ord-834f3bb4ba9245099dd540a794769c9b
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06821988B2

Reaction notes

Loading…