Dimethylformamide → 3-[3-(2-methoxyacetylamino)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide

HRID 1272929Notes

Reaction equation

HRID 1272929 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=3)[N:10]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:26][O:27][CH2:28][C:29](Cl)=[O:30].C(N(CC)CC)C.CN(C)C=O>O1CCCC1>[CH3:26][O:27][CH2:28][C:29]([NH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17]([NH2:19])=[O:18])[CH:15]=3)[N:10]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1)=[O:30]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 224799593-(3-Aminophenyl)-1-perhydro-2h-pyran-2-yl-1h-indazole5-carboxamide

Product 1

HCID 224801093-[3-(2-methoxyacetylamino)phenyl]-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carboxamide in tetrahydrofuran (6 mL), was added 2-methoxyacetyl chloride (0.065 mL, 0.713 mmol) followed by triethyl amine (0.414 mL, 2.97 mmol). A small volume of dimethyl formamide was added to aid solubility (1 mL). The reaction mixture was stirred at room temperature for 2 hours. The solvent was removed under reduced pressure and he crude was partitioned between ethyl acetate and water. The crude product was isolated as an oily yellow residue (yield not calculated): ES-MS (m/z) 409 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure and he crude
  2. customwas partitioned between ethyl acetate and water

Sources & evidence

ORD record
ord-212a371c5eb6483cb02ecfae8cea64da
Source dataset
uspto-grants-2007_04
Patent number
US07208513B2

Reaction notes

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