Water → HCID 66893273, compound

HRID 532823Notes

Reaction equation

ClC[C:3]1[N:4]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[S:6][CH:7]=1.Cl.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:18]=1[N:26]([CH2:31][CH2:32][CH3:33])[CH2:27][CH2:28][NH:29][CH3:30].C(=O)([O-])[O-].[Na+].[Na+].O>CN(C=O)C.C(OCC)(=O)C.CO>[CH3:15][O:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[C:18]=1[N:26]1[CH2:31][CH2:32][CH2:33][N:29]([CH2:30][C:7]2[S:6][C:5]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)=[N:4][CH:3]=2)[CH2:28][CH2:27]1

Participants

Conditions

Temperature: 45 °C

Procedure

4-(Chloromethyl)-2-phenyl-1,3-thiazole (300 mg, 1.5 mmol, 1 equiv), N-(2-methoxy-6-nitrophenyl)-N′-methyl-N-propylethane-1,2-diamine hydrochloride (all from step 1, 1 equiv), and sodium carbonate (300 mg, 2 equiv) were suspended in 5 mL of anhydrous DMF. The mixture was stirred at 45° C. for 2 hours. After cooling down to room temperature, ethyl acetate (100 mL) and water (50 mL) were added. The organic layer was subjected to flash chromatography (0 to 5% MeOH in ethyl acetate) to give 1-(2-methoxy-6-nitrophenyl)-4-(2-phenylthiazol-5-ylmethyl)-[1,4]diazepane (250 mg, 40%). MS (ES) m/z 425.1 (M+H+).

Workup

temperatureAfter cooling down to room temperature

Sources & evidence

ORD record: ord-3bc63b88c03a4732838acfede30372b3
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08853202B2

Reaction notes

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