Hydrochloric Acid → N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide

HRID 627894

Reaction equation

C([Li])CCC.Br[C:7]1[S:20][C:10]2[C:11]3[CH:19]=[N:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30].Cl.C([O-])(O)=O.[Na+]>CCCCCC.O1CCCC1>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29]([C:7]1[S:20][C:10]2[C:11]3[CH:19]=[N:18][CH:17]=[CH:16][C:12]=3[O:13][CH2:14][CH2:15][C:9]=2[CH:8]=1)=[O:30]

Participants

Conditions

Temperature: -78 °C

Procedure

1.6 M of n-Butyllithium in hexane (0.6302 mL) was added dropwise to a solution of 2-bromo-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepine (0.227 g, 0.804 mmol) in tetrahydrofuran (6.00 mL, 74.0 mmol) at −75° C. The dark brown mixture was stirred at −78° C. for 20 min. 1-Chloro-2-isocyanato-benzene (0.1421 g, 0.9252 mmol) in 2 ml of tetrahydrofuran was added dropwise and the mixture was kept at −78° C. for 20 min. 4N aq. HCl (1 ml) was added and the mixture was poured into 50 ml of sat. aq NaHCO3. The mixture was extracted twice with methylene chloride, combined, and washed with water and brine, and dried over MgSO4. After concentrating under vacuum, the residue was triturated with ethyl acetate. The collected precipitate was N-(2-chlorophenyl)-4,5-dihydropyrido[4,3-b]thieno[2,3-d]oxepin-2-carboxamide (0.19 g, 66% yield). MS (ESI+) 357.0.

Workup

waitthe mixture was kept at −78° C. for 20 min
extractionThe mixture was extracted twice with methylene chloride
washwashed with water and brine
dry with materialdried over MgSO4
concentrationAfter concentrating under vacuum
customthe residue was triturated with ethyl acetate

Sources & evidence

ORD record: ord-b12b3e17038846f5975d29d59f070792
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09309265B2

Linked notes

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