Sodium Azide → HCID 178445770, compound

HRID 713919Notes

Reaction equation

[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][NH:23][CH2:24][C:25]#[N:26])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[N-:27]=[N+:28]=[N-:29].[Na+].C([O-])(O)=O.[Na+]>O.C(O)(C)C.[Zn+2].[Br-].[Br-]>[NH:27]1[C:25]([CH2:24][NH:23][CH2:22][C:17]2[CH:16]=[CH:15][C:14]3[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]4[CH2:9][CH2:10][C@H:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:6][CH2:7]4)[CH:13]=3)[CH:18]=2)=[N:26][N:29]=[N:28]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 2-((6-((trans)-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methylamino)acetonitrile (240 mg, 0.69 mmol) in water and isopropanol (10 mL, 1:5) was added NaN3 (50 mg, 0.76 mmol, 1.1 eq) and ZnBr2 (153 mg, 0.69 mmol, 1.0 eq), then refluxed for 18 h. The reaction was cooled to 0° C. and saturated NaHCO3 was added. The mixture was extracted with DCM (20 mL×3) and the aqueous layer was destroyed by NaClO solution. The organic layer was concentrated and the residue was the title compound as a white solid (27 mg, yield: 11%). ESI-MS (M+H+): 394.3. HPLC: 91.15%, 1H NMR (400 MHz, CD3OD) δ: 7.82 (s, 1H), 7.79-7.72 (m, 2H), 7.42 (d, 1H), 7.16 (d, 2H), 4.47-4.31 (m, 5H), 2.26 (d, 2H), 1.89 (d, 2H), 1.45-1.41 (m, 2H), 1.24-1.09 (m, 3H), 0.88 (s, 9H).

Workup

temperaturerefluxed for 18 h
extractionThe mixture was extracted with DCM (20 mL×3)
customthe aqueous layer was destroyed by NaClO solution
concentrationThe organic layer was concentrated

Sources & evidence

ORD record: ord-b100f8eb2a2046bfa767d6a8cb88f4d3
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09186367B2

Reaction notes

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