Hydrochloric Acid → N-ethyl-7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxamide

HRID 525829Notes

Reaction equation

[CH3:1][C:2]1[CH:6]=[CH:5][O:4][C:3]=1[C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:26]=[CH:27][CH:28]=1)[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]2[CH:20]=[C:21]([C:23](O)=[O:24])[S:22][C:15]=12)=[O:8].C1C[N:32]([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)[CH2:31][CH2:30]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>[CH2:31]([NH:32][C:23]([C:21]1[S:22][C:15]2[C:16](=[N:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]2[CH:26]=[CH:27][CH:28]=[C:10]([NH:9][C:7]([C:3]3[O:4][CH:5]=[CH:6][C:2]=3[CH3:1])=[O:8])[CH:11]=2)[CH:20]=1)=[O:24])[CH3:30]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred, cooled (0° C.) solution of 7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxylic acid (120 mg, 0.30 mmol) in anhydrous DMF (10 ml) were added PyBOP (171 mg, 0.33 mmol) and N,N-diisopropylethylamine (85 mg, 0.66 mmol). The mixture was stirred at 0° C. for 5 minutes, followed by addition of 2M ethylamine solution in THF (0.18 ml, 0.36 mmol). Stirring was continued at 0° C. for another 40 minutes. The mixture was poured into 100 ml of water with vigorous stirring. 2M HCl was added dropwise until pH=5. The precipitates were filtered, washed with water and dried to give N-ethyl-7-{3-[(3-methyl-2-furoyl)amino]phenoxy}thieno[3,2-b]pyridine-2-carboxamide as light yellow solid. Yield: 115 mg, 90%.

Workup

stirringStirring
waitwas continued at 0° C. for another 40 minutes
filtrationThe precipitates were filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-28c53857df22408b929bddca3f376a45
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340555B2

Reaction notes

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