N,O-Dimethylhydroxylamine → HCID 45112604, compound

HRID 1170934Notes

Reaction equation

HRID 1170934 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([OH:12])=O)=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[CH3:13][NH:14][O:15][CH3:16].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:16][O:15][N:14]([CH3:13])[C:10]([C:6]1[CH:5]=[C:4]2[C:9](=[CH:8][CH:7]=1)[NH:1][CH:2]=[CH:3]2)=[O:12]

Participants

6

Reactant 4

HCID 14232N,O-DimethylhydroxylamineHCID 742801H-Indole-5-Carboxylic AcidHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Product 1

HCID 45112604HCID 45112604, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.483 g (3 mmol) 1H-Indole-5-carboxylic acid, 0.351 mg (3.6 mmol) N,O-dimethylhydroxylamine, 1.155 g (3.6 mmol) TBTU and 1.163 g (9 mmol) DIPEA in 15 mL DMF was stirred at room temperature for 2 h and evaporated. NaHCO3 aq. was added and the mixture was extracted with DCM. The combined organic layers were dried with MgSO4, evaporated and the title compound was used crude in the subsequent reaction.

Workup

  1. customevaporated
  2. additionNaHCO3 aq. was added
  3. extractionthe mixture was extracted with DCM
  4. dry with materialThe combined organic layers were dried with MgSO4
  5. customevaporated
  6. customin the subsequent reaction

Sources & evidence

ORD record
ord-87a9e68f8b1440169ffbba7629e8bd87
Source dataset
uspto-grants-2010_11
Patent number
US07829563B2

Reaction notes

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