Ammonium Chloride → HCID 86704415, compound

HRID 1748219Notes

Reaction equation

[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH:16]([F:18])[F:17])[C:5]=2[CH2:19][O:20][CH:21]2[CH2:27][CH:26]3[N:28]([C:29]4[CH:36]=[CH:35][C:32]([C:33]#[N:34])=[CH:31][C:30]=4[F:37])[CH:23]([CH2:24][CH2:25]3)[CH2:22]2)[CH2:3][CH2:2]1.[N-:38]=[N+:39]=[N-:40].[Na+].[Cl-].[NH4+]>CN(C)C(=O)C.C(OCC)(=O)C>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH:16]([F:17])[F:18])[C:5]=2[CH2:19][O:20][CH:21]2[CH2:22][CH:23]3[N:28]([C:29]4[CH:36]=[CH:35][C:32]([C:33]5[N:38]=[N:39][NH:40][N:34]=5)=[CH:31][C:30]=4[F:37])[CH:26]([CH2:25][CH2:24]3)[CH2:27]2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 120 °C

Procedure

4-(3-((5-cyclopropyl-3-(2-(difluoromethoxy)phenyl)isoxazol-4-yl)methoxy)-8-azabicyclo[3.2.1]octan-8-yl)-3-fluorobenzonitrile (70 mg, 0.14 mmol) was dissolved in N,N-dimethylacetamide (2 ml), sodium azide (91 mg, 10 eq, 1.40 mmol) and ammonium chloride (75 mg, 10 eq, 1.40 mmol) were added, and the mixture was stirred at 120° C. overnight. Upon cooling to room temperature, the reaction mixture was diluted with ethyl acetate (30 mL) and washed with brine (2×20 mL). The combined organics were separated, dried (MgSO4), and evaporated in vacuo. The product was purified by mass directed reverse phase HPLC to give a white solid.

Workup

temperatureUpon cooling to room temperature
washwashed with brine (2×20 mL)
customThe combined organics were separated
dry with materialdried (MgSO4)
customevaporated in vacuo
customThe product was purified by mass
customto give a white solid

Sources & evidence

ORD record: ord-677e408d2723424ab6b2f7f05f59e68e
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150568B2

Reaction notes

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