Ethylamine → N'-[4-(1,2,2,6,6-Pentamethyl-piperidin-4-ylcarbamoyl)-phenyl]-hydrazinecarboxylic acid tert-butyl ester

HRID 1160129

Reaction equation

HRID 1160129 reaction equation
[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:18]=[CH:17][C:13]([C:14]([OH:16])=O)=[CH:12][CH:11]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:46][CH:47]1[CH2:52][C:51]([CH3:54])([CH3:53])[N:50]([CH3:55])[C:49]([CH3:57])([CH3:56])[CH2:48]1>CC(N(C)C)=O>[C:1]([O:5][C:6]([NH:8][NH:9][C:10]1[CH:11]=[CH:12][C:13]([C:14](=[O:16])[NH:46][CH:47]2[CH2:48][C:49]([CH3:56])([CH3:57])[N:50]([CH3:55])[C:51]([CH3:54])([CH3:53])[CH2:52]2)=[CH:17][CH:18]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 6341EthylamineHCID 6937924-Amino-1,2,2,6,6-pentamethylpiperidineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 27559844-(2-(tert-Butoxycarbonyl)hydrazinyl)benzoic acid

Product 1

HCID 59515583N'-[4-(1,2,2,6,6-Pentamethyl-piperidin-4-ylcarbamoyl)-phenyl]-hydrazinecarboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 4-(N′-tert-Butoxycarbonyl-hydrazino)-benzoic acid (4.452 g) in DMA (30 ml) was added disopropyl ethyl amine (6.16 ml) and HBTU (6.69 g) with stirring at room temp. 4-Amino-1,2,2,6,6-pentamethylpiperidine (3 g) was then added to the stirred solution. Stirring continued at room temp for 4 hrs.

Workup

  1. stirringStirring

Sources & evidence

ORD record
ord-bea97ea435f440fe82eb8e6b2adb9c14
Source dataset
uspto-grants-2010_10
Patent number
US07816361B2

Linked notes

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