Ammonium Chloride → HCID 57471439, compound

HRID 510552Notes

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-f89a707587d94ce088d14584c47463dd
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096619B2

Reaction notes

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