N-Methylpropanamide → N-(7-[1,4]Dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-4-[(methyl-propionyl-amino)-methyl]-benzamide

HRID 2222169Notes

Reaction equation

[H-].[Na+].[CH3:3][NH:4][C:5](=[O:8])[CH2:6][CH3:7].Cl[CH2:10][C:11]1[CH:37]=[CH:36][C:14]([C:15]([NH:17][C:18]2[S:19][C:20]3[C:26]([CH:27]4[CH2:33][O:32][CH2:31][CH2:30][O:29][CH2:28]4)=[CH:25][CH:24]=[C:23]([O:34][CH3:35])[C:21]=3[N:22]=2)=[O:16])=[CH:13][CH:12]=1>O>[O:32]1[CH2:33][CH:27]([C:26]2[C:20]3[S:19][C:18]([NH:17][C:15](=[O:16])[C:14]4[CH:13]=[CH:12][C:11]([CH2:10][N:4]([CH3:3])[C:5](=[O:8])[CH2:6][CH3:7])=[CH:37][CH:36]=4)=[N:22][C:21]=3[C:23]([O:34][CH3:35])=[CH:24][CH:25]=2)[CH2:28][O:29][CH2:30][CH2:31]1

Participants

Conditions

Temperature: 55 °C

Procedure

Sodium hydride (4.8 mg, 60% disp. in mineral oil, 0.2 mmol) was added to N-methylpropionamide (1 ml, 11 mmol), followed by 4-chloromethyl-N-(7-[1,4]dioxepan-6-yl-4-methoxy-benzothiazol-2-yl)-benzamide (50 mg, 1.2 mmol) and the reaction mixture was heated to 55° C. for 3 hrs. After cooling, the mixture was diluted with water (5 ml) and extracted twice with ethyl acetate (5 ml). The combined organic phases were dried with magnesium sulfate, filtered and evaporated. Final purification with preparative HPLC and final dry-freezing afforded the title compound as white solid (23 mg, 42% yield). MS: m/e=484(M+H+).

Workup

temperatureAfter cooling
extractionextracted twice with ethyl acetate (5 ml)
dry with materialThe combined organic phases were dried with magnesium sulfate
filtrationfiltered
customevaporated
customFinal purification with preparative HPLC
customfinal dry-freezing

Sources & evidence

ORD record: ord-492c6abdba0f43e1889a7ffc49b6f2c5
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371748B2

Reaction notes

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