Ammonium Chloride → HCID 57471439, compound

HRID 1044534Notes

Reaction equation

[NH2:1][CH:2]1[CH:11]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:9]=[C:8]([O:19][CH2:20][CH2:21][NH:22][S:23]([CH2:26][CH:27]3[CH2:29][CH2:28]3)(=[O:25])=[O:24])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.[O:30]1[CH2:33][C:32](=O)[CH2:31]1.C([BH3-])#N.[Na+].[Cl-].[NH4+]>CO.[Cl-].[Zn+2].[Cl-]>[CH2:12]([CH:11]1[C:10]2[CH:9]=[C:8]([O:19][CH2:20][CH2:21][NH:22][S:23]([CH2:26][CH:27]3[CH2:29][CH2:28]3)(=[O:25])=[O:24])[CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3][CH:2]1[NH:1][CH:32]1[CH2:33][O:30][CH2:31]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 40 °C

Procedure

N-(2-(7-Amino-8-benzyl-5,6,7,8-tetrahydronaphthalen-2-yloxy)ethyl)-1-cyclopropylmethanesulfonamide (50 mg, 0.121 mmol) was dissolved in methanol. Oxetan-3-one (87 mg, 1.21 mmol), zinc chloride (66 mg, 0.482 mmol) and sodium cyanoborohydride (23 mg, 0.362 mmol) were added at 0° C. The reaction mixture was then heated to 40° C. for 5 h. Aqueous ammonium chloride solution was added and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel, dichloromethane, methanol). Yield: 3 mg (6.4 μmol, 5%).

Workup

extractionthe aqueous layer was extracted with ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography (silica gel, dichloromethane, methanol)

Sources & evidence

ORD record: ord-d2f57f6e13e04108839c99f0d3ed0620
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08563617B2

Reaction notes

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