Diethyl Ether → tert-butyl 2-[(2-([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)amino]ethylcarbamate

HRID 1247814Notes

Reaction equation

HRID 1247814 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C([O:14][C:15]1[C:16](=[O:47])[C:17](=O)[C:18]=1[NH:19][C:20]1[CH:21]=[N:22][N:23]([CH3:45])[C:24]=1[NH:25][C:26]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)C.C(N(CC)CC)C.C(OCC)C>C(O)C.CCCCCC>[CH3:45][N:23]1[C:24]([NH:25][C:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:20]([NH:19][C:18]2[C:15](=[O:14])[C:16](=[O:47])[C:17]=2[NH:1][CH2:2][CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:8])([CH3:10])[CH3:9])[CH:21]=[N:22]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamineHCID 219045093-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)amino}-3-cyclobutene-1,2-dione

Product 1

HCID 21904498tert-butyl 2-[(2-([1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)amino]ethylcarbamateYield 93.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

To a suspension of tert-butyl 2-aminoethylcarbamate (288 mg) and 3-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-cyclobutene-1,2-dione (718 mg) in ethanol (20 ml) was added triethylamine (0.209 ml), and the mixture was stirred under reflux for 4 hours. To the reaction mixture were added diethyl ether and hexane. The crystalline precipitate was collected by filtration and dried in vacuo to give tert-butyl 2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)amino]ethylcarbamate (830 mg) as a solid.

Workup

  1. temperatureunder reflux for 4 hours
  2. filtrationThe crystalline precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-cd576cc8aeb741fba99eee74fb2ebc17
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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