Acetic Anhydride → HCID 86732473, compound

HRID 1776445Notes

Reaction equation

HRID 1776445 reaction equation
[NH2:1][C:2]1[C:3]([Cl:34])=[C:4]([C:30]([Cl:33])=[CH:31][CH:32]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[N:20]=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)[C:18]([O:28][CH3:29])=[CH:17][N:16]=2)=[N:7]1.C(N(CC)CC)C.[C:42](OC(=O)C)(=[O:44])[CH3:43].C(=O)([O-])O.[Na+]>CN(C)C=O.C(OCC)(=O)C>[Cl:34][C:3]1[C:4]([CH2:5][N:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[C:8]([C:15]3[N:20]=[C:19]([NH:21][C:22]4[CH:23]=[CH:24][N:25]=[CH:26][CH:27]=4)[C:18]([O:28][CH3:29])=[CH:17][N:16]=3)=[N:7]2)=[C:30]([Cl:33])[CH:31]=[CH:32][C:2]=1[NH:1][C:42](=[O:44])[CH3:43]

Participants

7

Reactant 4

HCID 7918Acetic Anhydride2×HCID 8471Triethylamine2×HCID 516892Sodium BicarbonateHCID 86732472HCID 86732472, compound

Product 1

HCID 86732473HCID 86732473, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

50 mg of 2-[1-(3-amino-2,6-dichlorobenzyl)-1H-indazol-3-yl]-5-methoxy-N-(pyridin-4-yl)pyrimidin-4-amine (40-1, 0.102 mmol, 1.0 eq.) were dissolved in 0.6 ml of dry N,N-dimethylformamide. 0.014 ml N,N-diethylethanamine (0.102 mmol, 1.0 eq.) and 0.010 ml acetic anhydride (0.102 mmol, 1.0 eq.) were added at 0° C. and stirred for 3.5 h Then again 0.014 ml N,N-diethylethanamine (0.102 mmol, 1.0 eq.) and 0.010 ml acetic anhydride (0.102 mmol, 1.0 eq.) were added at 0° C. and stirred over night at room temperature. Saturated sodium hydrogen carbonate solution and ethyl acetate were added and the reaction mixture was stirred for 30 min. The organic layer was washed with ethyl acetate twice. The combined organic layers were dried over a silicone filter and concentrated in vacuum. The residue was purified by flash chromatography to yield 17.3 mg (0.03 mmol, 30%) of the analytically pure target compound.

Workup

  1. stirringstirred over night at room temperature
  2. stirringthe reaction mixture was stirred for 30 min
  3. washThe organic layer was washed with ethyl acetate twice
  4. dry with materialThe combined organic layers were dried over a silicone
  5. filtrationfilter
  6. concentrationconcentrated in vacuum
  7. customThe residue was purified by flash chromatography
  8. customto yield 17.3 mg (0.03 mmol, 30%) of the analytically pure target compound

Sources & evidence

ORD record
ord-e7727a46da114b668cb645eed043532a
Source dataset
uspto-grants-2016_02
Patent number
US09265763B2

Reaction notes

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