Hydrochloric Acid → HCID 178427867, compound

HRID 507083Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].Cl.C(N(CC)CC)C.[F:13][C:14]([F:52])([F:51])[C:15]1[CH:16]=[C:17]([CH:44]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:46]=1)[CH2:18][N:19]([C:42]#[N:43])[CH:20]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[C:22]2[C:33]([CH3:41])=[C:34]([C:37]([F:40])([F:39])[F:38])[CH:35]=[CH:36][C:21]1=2.Cl>C1(C)C=CC=CC=1.ClCCl>[F:50][C:47]([F:48])([F:49])[C:45]1[CH:44]=[C:17]([CH:16]=[C:15]([C:14]([F:52])([F:51])[F:13])[CH:46]=1)[CH2:18][N:19]([C:42]1[NH:43][N:3]=[N:2][N:1]=1)[CH:20]1[CH2:26][CH2:25][CH2:24][N:23]([C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28])[C:22]2[C:33]([CH3:41])=[C:34]([C:37]([F:38])([F:39])[F:40])[CH:35]=[CH:36][C:21]1=2

Participants

Conditions

Temperature: 110 °C

Procedure

Add sodium azide (42 mg, 0.64 mmol) and triethylamine hydrochloride (88 mg, 0.64 mmol) to a solution of (+/−)-isopropyl 5-[(3,5-bistrifluoromethyl-benzyl)-cyano-amino]-9-methyl-8-trifluormethyl-2,3,4,5-tetrahydrobenzo[b]azepine-1-carboxylate (124 mg, 0.21 mmol) in toluene (2 mL). Stir the mixture at 110° C. overnight. Cool down the mixture to room temperature, add 1N HCl (5 mL) and dichloromethane. Separate the layers, dry the organic phase over anhydrous magnesium sulfate, filter and remove the solvent under reduced pressure to provide 117 mg (89%) of the title compound. MS (ES−): 623 (M−H).

Workup

temperatureCool down the mixture to room temperature
customSeparate the layers
dry with materialdry the organic phase over anhydrous magnesium sulfate
filtrationfilter
customremove the solvent under reduced pressure

Sources & evidence

ORD record: ord-567408e932874af8a52086bb3c617f8c
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07786108B2

Reaction notes

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