Potassium Carbonate → HCID 86709787, compound

HRID 1529408Notes

Reaction equation

HRID 1529408 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[C:22]#[C:23][Si](C)(C)C)=[CH:13][CH:14]=2)[C:9]([C:28]2[N:33]=[C:32]([O:34][C@H:35]3[CH2:42][N:41]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:40][CH2:39][C:36]43[CH2:38][CH2:37]4)[CH:31]=[N:30][CH:29]=2)=[N:8]1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O>[C:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[N:8]=[C:9]2[C:28]1[N:33]=[C:32]([O:34][C@H:35]2[CH2:42][N:41]([C:43]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[O:44])[CH2:40][CH2:39][C:36]32[CH2:38][CH2:37]3)[CH:31]=[N:30][CH:29]=1)#[CH:23]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67960123HCID 67960123, compound

Product 1

HCID 86709787HCID 86709787, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (4R)-tert-butyl 4-(6-(1-(tetrahydro-2H-pyran-2-yl)-5-(2-((trimethylsilyl)ethynyl)phenyl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (110 mg, 0.162 mmol) and potassium carbonate (112 mg, 0.811 mmol) in MeOH (1623 μL) was stirred at RT for 2 h. The mixture was diluted with EtOAc (150 ml), added to a separatory funnel, and washed with water (2×100 ml) before the organic layer was separated, dried over Na2SO4, and concentrated to give (4R)-tert-butyl 4-(6-(5-(2-ethynylphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-3-yl)pyrazin-2-yloxy)-6-azaspiro[2.5]octane-6-carboxylate (80 mg, 0.132 mmol, 81% yield) as a yellowish oil. MS (ESI, pos. ion) m/z: 606.2 (M+1).

Workup

  1. additionadded to a separatory funnel
  2. washwashed with water (2×100 ml) before the organic layer
  3. customwas separated
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9e201c103d954167ab1fd2c7d79421e1
Source dataset
uspto-grants-2015_07
Patent number
US09090593B2

Reaction notes

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