Hydrochloric Acid → 4-(5-Nitro-benzooxazol-2-YL)-1,4-diaza-bicyclo[3.2.2]nonane

HRID 1815765Notes

Reaction equation

CS[C:3]1[O:4][C:5]2[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][C:6]=2[N:7]=1.[NH2:15][C:16]1[CH:21]=[C:20]([N+:22]([O-])=O)[CH:19]=[CH:18]C=1O.Cl.[C:27](OCC)(=O)[CH3:28]>>[N+:12]([C:9]1[CH:10]=[CH:11][C:5]2[O:4][C:3]([N:22]3[CH:20]4[CH2:21][CH2:16][N:15]([CH2:18][CH2:19]4)[CH2:28][CH2:27]3)=[N:7][C:6]=2[CH:8]=1)([O-:14])=[O:13]

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 8857Ethyl Acetate2×

HCID 36133892-Amino-4-Nitrophenol

HCID 152521182-(Methylthio)-5-nitrobenzo[d]oxazole

Product 1

HCID 224958014-(5-Nitro-benzooxazol-2-YL)-1,4-diaza-bicyclo[3.2.2]nonaneYield 36%

Procedure

The title compound was prepared from 2-methylsulfanyl-5-nitro-benzooxazole (prepared from 2-amino-4-nitrophenol by the methods described in Example 5 and Example 7) by the procedure described in Example 9 in 36% yield: 1H NMR CDCl3, 400 MHz) δ 7.84 (d, 1H, J=2.1 Hz), 7.97 (dd, 1H, J=8.7, 2.1 Hz), 7.28 (d, 1H, J=8.7 Hz), 4.56-4.55 (m, 1H), 3.97 (t, 2H, J=5.8 Hz), 3.23-3.16 (m, 4H), 3.08-3.01 (m, 2H), 2.23-2.15 (m, 2H), 1.94-1.85 (m, 2H); 13C NMR CDCl3, 100 MHz) δ 163.1, 152.8, 145.2, 144.3, 117.2, 111.7, 108.5, 56.4, 50.5, 45.9, 43.8, 26.3; MS (Cl) m/z 289.2 (M+1); HPLC retention time=3.11 min. The hydrochloride salt was prepared by diluting in ethyl acetate and adding a 2.5 N HCl solution in ethyl acetate: mp=240.2° C.

Sources & evidence

ORD record: ord-eb949e5dc9094b81b9c1ad6051c3d4a4
Source dataset: uspto-grants-2005_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06881734B2

Reaction notes

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