Diethyl Ether → tert-butyl {3-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxo-1-cyclobuten-1-yl)amino]propyl)carbamate

HRID 1247816Notes

Reaction equation

HRID 1247816 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].C([O:15][C:16]1[C:17](=[O:48])[C:18](=O)[C:19]=1[NH:20][C:21]1[CH:22]=[N:23][N:24]([CH3:46])[C:25]=1[NH:26][C:27]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)C.C(N(CC)CC)C.C(OCC)C>C(O)C.CCCCCC>[CH3:46][N:24]1[C:25]([NH:26][C:27]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:21]([NH:20][C:19]2[C:16](=[O:15])[C:17](=[O:48])[C:18]=2[NH:1][CH2:2][CH2:3][CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH:22]=[N:23]1

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 219045093-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)amino}-3-cyclobutene-1,2-dione

Product 1

HCID 86593407tert-butyl {3-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxo-1-cyclobuten-1-yl)amino]propyl)carbamateYield 927.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

To a suspension of tert-butyl 3-aminopropylcarbamate (366 mg) and 3-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-cyclobutene-1,2-dione (67.0 mg) in ethanol (30 ml) was added triethylamine (0.195 ml), and the mixture was stirred under reflux for 3 hours. To the reaction mixture were added diethyl ether (40 ml) and hexane (10 ml). The crystalline precipitate was collected by filtration and dried in vacuo to give tert-butyl {3-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxo-1-cyclobuten-1-yl)amino]propyl}carbamate (788 mg) as a solid.

Workup

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

Sources & evidence

ORD record
ord-b331c77bd6a5478ca035b70e4c123c95
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

Loading…