Hydrochloric Acid → N-ethyl-7-(3-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)thieno[3,2-b]pyridine-2-carboxamide

HRID 525836Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[NH:9][C:10]([C:12]1[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=1)[O:15][C:16]1[CH:21]=[CH:20][N:19]=[C:18]2[CH:22]=[C:23]([C:25](O)=[O:26])[S:24][C:17]=12)=[O:11].C1C[N:34]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:33][CH2:32]1.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.C(N)C.C1COCC1.Cl>CN(C=O)C.O>[CH2:33]([NH:34][C:25]([C:23]1[S:24][C:17]2[C:18](=[N:19][CH:20]=[CH:21][C:16]=2[O:15][C:14]2[CH:28]=[CH:29][CH:30]=[C:12]([C:10]([NH:9][C:3]3[CH:4]=[C:5]([CH3:8])[CH:6]=[CH:7][C:2]=3[F:1])=[O:11])[CH:13]=2)[CH:22]=1)=[O:26])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred, cooled (0° C.) solution of 7-(3-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)thieno[3,2-b]pyridine-2-carboxylic acid (120 mg, 0.28 mmol) in anhydrous DMF (10 ml) were added PyBOP (161 mg, 0.31 mmol) and N,N-diisopropylethylamine (72 mg, 0.56 mmol). The mixture was stirred at 0° C. for 5 minutes, followed by addition of 2M ethylamine solution in THF (0.2 ml, 0.4 mmol). Stirring was continued at 0° C. for another 30 minutes. The mixture was poured into 100 ml of water with vigorous stirring. 2M HCl was added dropwise until pH=4. The precipitates were filtered, washed with water and dried to give N-ethyl-7-(3-{[(2-fluoro-5-methylphenyl)amino]carbonyl}phenoxy)thieno[3,2-b]pyridine-2-carboxamide as yellow solid. Yield: 112 mg, 88%.

Workup

stirringStirring
waitwas continued at 0° C. for another 30 minutes
filtrationThe precipitates were filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-fd16b8aa9d464c7a9dfe07807394e9d5
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340555B2

Reaction notes

Loading…