Diethyl Ether → di-tert-butyl 7-[({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-6,8-dioxo-2,5,9,12-tetraazatridecanedioate

HRID 459655Notes

Reaction equation

HRID 459655 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[C:5]([NH:27][C:28](=O)[O:29]C2C=CC=CC=2)[CH:4]=[N:3]1.[NH2:37][CH:38]([C:52](=[O:64])[NH:53][CH2:54][CH2:55][NH:56][C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C:39](=[O:51])[NH:40][CH2:41][CH2:42][NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45].C(N(C(C)C)C(C)C)C.C(OCC)C>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[C:5]([NH:27][C:28]([NH:37][CH:38]([C:52](=[O:64])[NH:53][CH2:54][CH2:55][NH:56][C:57]([O:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[O:58])[C:39](=[O:51])[NH:40][CH2:41][CH2:42][NH:43][C:44]([O:46][C:47]([CH3:50])([CH3:49])[CH3:48])=[O:45])=[O:29])[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 81531DiisopropylethylamineHCID 18442407Di-tert-butyl 7-amino-6,8-dioxo-2,5,9,12-tetraazatridecanedioateHCID 21904567Phenyl [1-methyl-5-(tritylamino)pyrazol-4-yl]carbamate

Product 1

HCID 18442406di-tert-butyl 7-[({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-6,8-dioxo-2,5,9,12-tetraazatridecanedioateYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of phenyl N-[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]carbamate (949 mg) and di-tert-butyl 7-amino-6,8-dioxo-2,5,9,12-tetraazatridecanedioate (968 mg) in dehydrated chloroform (4 ml) was added N-ethyldiisopropylamine (0.342 ml), and the mixture was stirred under reflux for 5 hours. To the reaction mixture was added diethyl ether. The resulting precipitate was collected by filtration and dried in vacuo to give di-tert-butyl 7-[({[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}carbonyl)amino]-6,8-dioxo-2,5,9,12-tetraazatridecanedioate (1.38 g) as a solid.

Workup

  1. temperatureunder reflux for 5 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. customdried in vacuo

Sources & evidence

ORD record
ord-0ebfaded5a274367a62b30ee1c5bb023
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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