Hydrochloric Acid → HCID 89401848, compound

HRID 1487000Notes

Reaction equation

HRID 1487000 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([C:13]2[N:17]=[CH:16][N:15](/[CH:18]=[CH:19]\[C:20]([NH:22][CH:23]3[CH:28]4[CH:24]3[CH2:25][N:26](C(OC(C)(C)C)=O)[CH2:27]4)=[O:21])[N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.O1CCOCC1.[ClH:44]>C(Cl)Cl>[ClH:44].[CH:24]12[CH:23]([NH:22][C:20](=[O:21])/[CH:19]=[CH:18]\[N:15]3[CH:16]=[N:17][C:13]([C:5]4[CH:4]=[C:3]([C:2]([F:1])([F:36])[F:37])[CH:8]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:6]=4)=[N:14]3)[CH:28]1[CH2:27][NH:26][CH2:25]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 89402063HCID 89402063, compound

Product 1

HCID 89401848HCID 89401848, compoundYield 37.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(Z)-tert-butyl 6-(3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylamido)-3-azabicyclo[3.1.0]hexane-3-carboxylate (0.05 g, 1.0 eq.) was dissolved in DCM (3 mL) and cooled to 0° C. where dioxane:HCl (0.2 mL) was added dropwise and stirred for 30 min. The reaction was allowed to warm to room temperature and stirred for 30 min, concentrated under reduced pressure. The crude product was triturated with ether to afford (Z)—N-(3-azabicyclo[3.1.0]hexan-6-yl)-3-(3-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,4-triazol-1-yl)acrylamide hydrochloride (0.015 g, 37.5% yield). 1H NMR (400 MHz, DMSO) δ, 9.61 (s, 1H), 8.75 (s, 2H), 8.60 (s, 2H), 8.30 (s, 1H), 7.38-7.40 (d, J=10.4 Hz, 1H), 5.87-5.89 (d, J=10.4 Hz, 1H), 2.91 (s, 1H), 2.14 (s, 2H), 1.23 (s, 3H); LCMS for Chemical Formula: C18H16F6N5O [M+H]+ 432.34 found 432.19 at retention time 2.302 min.

Workup

  1. stirringstirred for 30 min
  2. concentrationconcentrated under reduced pressure
  3. customThe crude product was triturated with ether

Sources & evidence

ORD record
ord-6d85114ffc8b41bfbd7149c93afed845
Source dataset
uspto-grants-2016_08
Patent number
US09428490B2

Reaction notes

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