Hydrochloric Acid → HCID 178461412, compound
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]#[C:10][CH2:11][CH2:12][N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[CH3:18])=[C:6]([NH2:8])[CH:7]=1.Cl.[N:20]([O-])=O.[Na+].[OH2:24]>>[Br:1][C:2]1[CH:7]=[C:6]2[C:5]([C:9]([OH:24])=[C:10]([CH2:11][CH2:12][N:13]3[CH2:17][CH2:16][CH2:15][C@H:14]3[CH3:18])[N:20]=[N:8]2)=[CH:4][CH:3]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of Example 168C (0.10 g, 0.325 mmol) in 2 mL of water was added 1.5 mL 6 M HCl. The resulting solution was cooled to 0° C. and NaNO2 (0.034 g, 0.488 mmol), dissolved in 1 mL water, was added dropwise. The resulting mixture was stirred for 30 minutes at 0° C. and subsequently heated to 90° C. for one hour. After cooling, contents were filtered and the precipitate was washed with 10 mL water and dried under reduced pressure to provide the product in 47% yield as a brown solid in HCl salt form, which was used without further purification. 1H NMR (CD3OD, 300 MHz) δ 8.10 (d, J=9 Hz, 1H), 7.82 (d, J=3 Hz, 1H), 7.60 (dd, J=3, 9 Hz, 1H), 3.89–3.76 (m, 2H), 3.58–3.53 (m, 1H) 3.42–3.23 (m, 4H), 2.38–2.30 (m, 1H), 2.16–2.06 (m, 2H), 1.83–1.75 (m, 1H), 1.51 (d, J=6 Hz, 3H). MS (ESI) [M]+ at 336.
Workup
- additionwas added dropwise
- temperaturesubsequently heated to 90° C. for one hour
- temperatureAfter cooling
- filtrationcontents were filtered
- washthe precipitate was washed with 10 mL water
- customdried under reduced pressure
- customto provide the product in 47% yield as a brown solid in HCl salt form, which
- customwas used without further purification
Sources & evidence
- ORD record
- ord-5210a7a94a3945ae86f271c04fc36674
- Source dataset
- uspto-grants-2006_12
- Patent number
- US07153889B2
Reaction notes
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