Acetic Anhydride → 1-(9-((5-chloro-2-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)ethanone

HRID 1056644Notes

Reaction equation

HRID 1056644 reaction equation
[CH2:1]1[C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[CH2:5][CH2:4][CH:3]([NH:12][C:13]2[C:18]([Cl:19])=[CH:17][N:16]=[C:15]([NH:20][C:21]3[CH:22]=[CH:23][C:24]4[C:28]([CH:29]=3)=[N:27][N:26]([CH3:30])[C:25]=4[CH3:31])[N:14]=2)[CH2:2]1.C(N(CC)CC)C.[C:39](OC(=O)C)(=[O:41])[CH3:40]>C(Cl)Cl>[Cl:19][C:18]1[C:13]([NH:12][CH:3]2[CH2:4][CH2:5][C:6]3([CH2:7][CH2:8][N:9]([C:39](=[O:41])[CH3:40])[CH2:10][CH2:11]3)[CH2:1][CH2:2]2)=[N:14][C:15]([NH:20][C:21]2[CH:22]=[CH:23][C:24]3[C:28]([CH:29]=2)=[N:27][N:26]([CH3:30])[C:25]=3[CH3:31])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 118390164N4-(9-azaspiro[5.5]undecan-3-yl)-5-chloro-N2-(2,3-dimethylindazol-6-yl)pyrimidine-2,4-diamine

Product 1

HCID 1183901731-(9-((5-chloro-2-((2,3-dimethyl-2H-indazol-6-yl)amino)pyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of N4-(9-azaspiro[5.5]undecan-3-yl)-5-chloro-N2-(2,3-dimethylindazol-6-yl)pyrimidine-2,4-diamine (0.10 g, 0.23 mmol) in anhydrous DCM (10.0 mL) were added N,N-diethylethanamine (0.036 g, 0.35 mmol) and acetyl acetate (0.029 g, 0.29 mmol). The mixture was stirred at room temperature for 30 min then diluted with DCM (40 mL), washed with water (20 mL×2), followed by saturated NaHCO3 (20 mL) and brine (20 mL), then dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1 to 15/1) to give the title compound as a light green solid (75 mg, 68%).

Workup

  1. washwashed with water (20 mL×2)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1 to 15/1)

Sources & evidence

ORD record
ord-086609e477e34a639a3a01fba4108b4e
Source dataset
uspto-grants-2016_07
Patent number
US09399637B2

Reaction notes

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