Isopropanol → HCID 67959906, compound

HRID 1529412Notes

Reaction equation

HRID 1529412 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13](C1CCCCO1)[N:12]=[C:11]2[C:23]1[N:28]=[C:27]([O:29][C@H:30]2[CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35][CH2:34][C:31]32[CH2:33][CH2:32]3)[CH:26]=[N:25][CH:24]=1)(C)([CH3:3])[CH3:2].CC(O)C>Cl>[CH2:32]1[C:31]2([CH2:34][CH2:35][NH:36][CH2:37][C@@H:30]2[O:29][C:27]2[N:28]=[C:23]([C:11]3[C:10]4[C:14](=[CH:15][CH:16]=[C:8]([CH2:7][C:6]([O:5][CH:1]([CH3:3])[CH3:2])=[O:45])[CH:9]=4)[NH:13][N:12]=3)[CH:24]=[N:25][CH:26]=2)[CH2:33]1

Participants

4

Reactant 2

HCID 3776IsopropanolHCID 67960475HCID 67960475, compound

Product 1

HCID 67959906HCID 67959906, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of (4R)-tert-butyl 4-((6-(5-(2-(tert-butoxy)-2-oxoethyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yl)oxy)-6-azaspiro[2.5]octane-6-carboxylate (280 mg, 0.452 mmol) in hydrogen chloride in IPA (9036 μl, 45.2 mmol) was stirred at 80° C. for 2 h. The mixture was concentrated and was diluted with EtOAc (150 ml), added to a separatory funnel, and washed with 1 N NaOH (2×75 ml) before the organic layer was separated, dried over Na2SO4, and concentrated to give (R)-isopropyl 2-(3-(6-(6-azaspiro[2.5]octan-4-yloxy)pyrazin-2-yl)-1H-indazol-5-yl)acetate (180 mg, 0.427 mmol, 95% yield) and was used as is. MS (ESI, pos. ion) m/z: 422.1 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. additionwas diluted with EtOAc (150 ml)
  3. additionadded to a separatory funnel
  4. washwashed with 1 N NaOH (2×75 ml) before the organic layer
  5. customwas separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-df0348e09e3546e99c30c2723cf818e5
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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