Triethylamine → HCID 18367769, compound

HRID 379820Notes

Reaction equation

HRID 379820 reaction equation
[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15]([OH:17])=O)(=[O:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.Cl.[CH3:36][NH:37][O:38][CH3:39].C(N(CC)CC)C>CN(C)C=O.O>[C:1]([NH:4][C:5]1[C:13]2[C:8](=[CH:9][C:10]([Cl:14])=[CH:11][CH:12]=2)[NH:7][C:6]=1[C:15]([N:37]([O:38][CH3:39])[CH3:36])=[O:17])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 199401P,P-Diphenylphosphinic azideHCID 18367851HCID 18367851, compound

Product 1

HCID 18367769HCID 18367769, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a mixture of (3-acetylamino-6-chloroindole)-2-carboxylic acid (step 3; 280 mg, 1.11 mmol), diphenyl phosphoryl azide (365 mg, 1.33 mmol) and N,O-dimethylhydroxylamine hydrochloride (162 mg, 1.66 mmol) in dimethylformamide (5 ml) was added triethylamine (0.58 ml, 4.16 mmol). After stirring for 1 h, the mixture was poured into water (10 ml) and extracted with diethyl ether (30 ml×2). The combined organic extracts were washed consecutively with water (20 ml×2), saturated sodium bicarbonate (20 ml), brine (20 ml), then dried (MgSO4). Removal of solvent gave the title compound as a brown solid (ca. 20%) which was used in the next step without further purification.

Workup

  1. extractionextracted with diethyl ether (30 ml×2)
  2. washThe combined organic extracts were washed consecutively with water (20 ml×2), saturated sodium bicarbonate (20 ml), brine (20 ml)
  3. dry with materialdried (MgSO4)
  4. customRemoval of solvent

Sources & evidence

ORD record
ord-38e5e368daaf491b958b8c117e91f479
Source dataset
uspto-grants-2001_10
Patent number
US06300363B1

Reaction notes

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