Acetic Anhydride → HCID 44470227, compound

HRID 2382955Notes

Reaction equation

HRID 2382955 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)[C:17]=3[CH:18]=[CH:19][CH:20]=2)=[O:11])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[C:37](OC(=O)C)(=[O:39])[CH3:38]>CN(C=O)C.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[C:37]([NH:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([C:12]2[C:13]3[CH:14]=[N:15][N:16]([C:21]4[CH:22]=[CH:23][C:24]([F:27])=[CH:25][CH:26]=4)[C:17]=3[CH:18]=[CH:19][CH:20]=2)=[O:11])=[CH:4][CH:3]=1)(=[O:39])[CH3:38]

Participants

7

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 58138817HCID 58138817, compound

Product 1

HCID 44470227HCID 44470227, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A chilled (0° C.) solution of 1-(4-fluoro-phenyl)-1H-indazole-4-carboxylic acid (6-amino-pyridin-3-ylmethyl)-amide (40.0 mg, 0.111 mmol) in DMF (1 mL) was treated with 4-dimethylaminopyridine (1 mg, 0.01 mmol), DIEA (0.39 mL, 2.2 mmol) and acetic anhydride (0.062 mL, 0.66 mmol). The mixture was allowed to gradually warm to room temperature. The solution was diluted with ethyl acetate (30 mL) and washed with saturated aqueous NH4Cl (3×10 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography, eluting with a gradient of 70-100% ethyl acetate in hexanes to afford the title compound as a white solid.

Workup

  1. washwashed with saturated aqueous NH4Cl (3×10 mL), saturated aqueous NaHCO3 (20 mL) and brine (20 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with a gradient of 70-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-18b1146d443b4d8b92011d62fac09a0b
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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