Dichloromethane methanol → HCID 67981451, compound

HRID 1520051Notes

Reaction equation

HRID 1520051 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:29]=[CH:28][C:18]([CH2:19][NH:20]C(=O)OC(C)(C)C)=[CH:17][CH:16]=3)[CH:14]=2)=[N:2]1.C(Cl)[Cl:31].CO>Cl.O1CCOCC1>[ClH:31].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[N:11]=[N:12][N:13]([C:15]3[CH:29]=[CH:28][C:18]([CH2:19][NH2:20])=[CH:17][CH:16]=3)[CH:14]=2)=[N:2]1

Participants

5

Reactant 2

HCID 21226129Dichloromethane methanolHCID 68060880HCID 68060880, compound

Product 1

HCID 67981451HCID 67981451, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl {4-[4-(1H-indazol-3-yl)-1H-1,2,3-triazol-1-yl]benzyl}carbamate (1.17 g; 3.00 mmol; 1.0 eq.) in HCl solution in 1,4-dioxane (7.5 mL, 4N) was stirred at RT. After 48 h, the reaction mixture was concentrated to dryness affording a sticky solid, which was sonicated in a 1:1 mixture of DCM/MeOH. The suspension obtained was concentrated to dryness to afford the title compound as a beige solid (967 mg, 98%). HPLC (Condition A): Rt 2.08 min (purity 95.3%). MS (ESI+): 291.1, MS (ESI−): 289.2. Purification by preparative HPLC of 50 mg of this crude by afforded a pure sample (35 mg): 1H NMR (300 Mz, DMSO-d6) δ: 13.40 (brs, 1H), 9.33 (s, 1H), 8.36 (dt, J=8.2 Hz, J=1.0 Hz, 1H), 8.07 (d, J=8.5 Hz, 2H), 7.68 (d, J=8.5 Hz, 2H), 7.62 (dt, J=8.2 Hz, 1.0 Hz, 1H), 7.47-7.42 (m, 1H), 7.29-7.24 (m, 1H), 4.02 (s, 2H). HPLC (Condition A): Rt 2.06 min (purity 97.5%). MS (ESI+): 291.1, MS (ESI−): 289.1.

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. customaffording a sticky solid, which
  3. customThe suspension obtained
  4. concentrationwas concentrated to dryness

Sources & evidence

ORD record
ord-8abe9b50515b4daca4e9a23fa73591f3
Source dataset
uspto-grants-2015_07
Patent number
US09073892B2

Reaction notes

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