Diisopropylethylamine → HCID 15550598, compound

HRID 1699521Notes

Reaction equation

HRID 1699521 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8](C(N=[N+]=[N-])=O)=[CH:7]1)=[O:5])[CH3:2].[C:20]([OH:23])(=O)C.[NH2:24][CH:25]([C:29]([C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:30])[C:26]([NH2:28])=[O:27].C([N:42](C(C)C)C(C)C)C>C1C=CC=CC=1.C1COCC1>[C:26]([CH:25]([NH:24][C:20](=[O:23])[NH:42][C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:7]=1)[C:29]([C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)=[O:30])(=[O:27])[NH2:28]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 12243795HCID 12243795, compoundHCID 18320699HCID 18320699, compound

Product 1

HCID 15550598HCID 15550598, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.10 g (4.27 mmol) of 3-azidocarbonyi-indole-1-carboxylic acid ethyl ester (Suvorov et al. Khimiya Gereotsiklicheskikh Soedinenii, 8 (1975) 1099-1105) in 15 ml of absolute benzene was heated reflux for 6 hours under nitrogen. After cooling to room temperature the benzene solution was rapidly added to a freshly prepared suspension of 2.04 g (4.27 mmol) of the product of step c) and 0.55 g (4.27 mmol) of ethyldiisopropylamine in 20 ml of THF.

Workup

  1. temperaturereflux for 6 hours under nitrogen

Sources & evidence

ORD record
ord-29442a5a83d74c35af1737d0e54b905d
Source dataset
uspto-grants-2002_02
Patent number
US06346625B1

Reaction notes

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