2-(Dimethylamino)acetohydrazide → HCID 178483332, compound

HRID 1353928Notes

Reaction equation

HRID 1353928 reaction equation
O1C2C=CC=CC=2C=C1[C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=2)[N:12]([CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[N:11]=1.[NH2:27][NH:28][C:29](=O)[CH2:30][N:31]([CH3:33])[CH3:32].[CH3:35][O-:36].[Na+]>CO.ClCCl>[O:36]1[C:15]2[CH:14]=[CH:13][CH:18]=[CH:17][C:16]=2[CH:19]=[C:35]1[CH:26]1[CH2:25][CH2:24][CH2:23][O:22][CH:21]1[N:12]1[C:13]2[C:18](=[CH:17][C:16]([C:19]3[NH:27][N:28]=[C:29]([CH2:30][N:31]([CH3:33])[CH3:32])[N:20]=3)=[CH:15][CH:14]=2)[CH:10]=[N:11]1

Participants

6

Reactant 3

HCID 683192-(Dimethylamino)acetohydrazide2×HCID 10942334Sodium MethoxideHCID 224798583-benzo[b]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile

Product 1

HCID 178483332HCID 178483332, compoundYield 7%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 6344DichloromethaneSolvent

Conditions

Temperature
100 °C

Procedure

To a suspension of 3-benzo[d]furan-2-yl-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (167 mg, 0.49 mmol) and N-amino-2-(dimethylamino)acetamide (171 mg, 1.46 mmol) in anhydrous methanol (1.0 mL) in a screw-top pressure tube was added sodium methoxide (445 μL of a 25% w/w in methanol). The tube was sealed and heated in a 100° C. oil bath for 21 h. An additional amount of N-amino-2-(dimethylamino)acetamide (171 mg, 1.46 mmol) was added and the reaction heated for an additional 2 days. The reaction was cooled, evaporated to dryness and partitioned between ethyl acetate and satd. ammonium chloride. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo to give a yellow solid. Purification of the residue by flash chromatography on silica gel using 5% methanol in dichloromethane then 20% methanol in dichloromethane gave the desired product (15 mg, 7% yield) as a pale yellow foam. ES-MS (m/z) 443 [M+H]+.

Workup

  1. customThe tube was sealed
  2. temperaturethe reaction heated for an additional 2 days
  3. temperatureThe reaction was cooled
  4. customevaporated to dryness
  5. custompartitioned between ethyl acetate and satd
  6. customThe organic layer was separated
  7. washwashed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customto give a yellow solid
  11. customPurification of the residue by flash chromatography on silica gel using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-5ed695cb59b648c085abf422cf4ad3f9
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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