Ammonium Chloride → HCID 178488678, compound

HRID 2240153Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:22][C@@H:23]1[CH2:27][CH2:26][O:25][CH2:24]1.[N-:28]=[N+:29]=[N-:30].[Na+].[Cl-].[NH4+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:13]([C:14]3[CH:15]=[CH:16][C:17]([C:18]4[NH:30][N:29]=[N:28][N:19]=4)=[CH:20][CH:21]=3)[N:12]=[CH:11][CH:10]=2)=[CH:5][C:4]=1[O:22][C@@H:23]1[CH2:27][CH2:26][O:25][CH2:24]1

Participants

Conditions

Temperature: 110 °C

Procedure

4-(5-{4-Methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)benzonitrile (40.0 mg, 0.111 mmol), sodium azide (35.82 mg, 0.5510 mmol), ammonium chloride (29.5 mg, 0.552 mmol), and 1 mL of N,N-dimethylformamide were mixed in a 500 mL flask and heated under an atmosphere of N2 at 110° C. for 6 hours. The mixture was cooled to room temperature and poured into 5 mL of ice cold 3.0 M aqueous HCl. The precipitate was collected by vacuum filtration and washed with several portions of water. The solid was dried in vacuo overnight to give 20 mg (0.044 mmol, 40%) of 5-[4-(5-{4-methoxy-3-[(3R)-tetrahydrofuran-3-yloxy]phenyl}-1H-pyrazol-1-yl)phenyl]-1H-tetrazole as a yellow solid. LC/MS (EI) tR 3.52, m/z 405.1 (M++1) 1H NMR (CDCl3 300 MHz) δ 2.0 (m, 2H); 3.7-3.9 (m, 4H); 3.9 (s, 3H); 4.8 (m, 1H); 6.6 (s, 2H); 7.0 (d, 1H); 7.1 (d, 1H); 7.4 (d, 2H); 7.8 (d, 2H); 7.8 (s, 1H).

Workup

temperatureThe mixture was cooled to room temperature
filtrationThe precipitate was collected by vacuum filtration
washwashed with several portions of water
customThe solid was dried in vacuo overnight

Sources & evidence

ORD record: ord-1fbe68a448d24e59a9c4f5b1491e87d3
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723348B2

Reaction notes

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