Triethylamine → di-tert-butyl (2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)amino]-1,3-propanediyl}biscarbamate

HRID 459658Notes

Reaction equation

HRID 459658 reaction equation
[NH2:1][CH:2]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C([O:23][C:24]1[C:25](=[O:56])[C:26](=O)[C:27]=1[NH:28][C:29]1[CH:30]=[N:31][N:32]([CH3:54])[C:33]=1[NH:34][C:35]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)C.C(N(CC)CC)C>C(O)C>[CH3:54][N:32]1[C:33]([NH:34][C:35]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:29]([NH:28][C:27]2[C:24](=[O:23])[C:25](=[O:56])[C:26]=2[NH:1][CH:2]([CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH:30]=[N:31]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15186003tert-butyl N-(2-amino-3-{[(tert-butoxy)carbonyl]amino}propyl)carbamateHCID 219045093-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl)amino}-3-cyclobutene-1,2-dione

Product 1

HCID 86597906di-tert-butyl (2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)amino]-1,3-propanediyl}biscarbamateYield 84.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of di-tert-butyl (2-amino-1,3-propanediyl)biscarbamate (810 mg) and 3-ethoxy-4-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-cyclobutene-1,2-dione (957 mg) in ethanol (10 ml) was added triethylamine (0.279 ml), and the mixture was stirred under reflux for 1 day. The reaction mixture was concentrated to about 5 ml in vacuo. To the concentrate was added diisopropyl ether. The precipitated crystals were collected by filtration and dried in vacuo to give di-tert-butyl {2-[(2-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3,4-dioxocyclobut-1-en-1-yl)amino]-1,3-propanediyl}biscarbamate (1.22 g) as a solid.

Workup

  1. temperatureunder reflux for 1 day
  2. concentrationThe reaction mixture was concentrated to about 5 ml in vacuo
  3. additionTo the concentrate was added diisopropyl ether
  4. filtrationThe precipitated crystals were collected by filtration
  5. customdried in vacuo

Sources & evidence

ORD record
ord-a5ff968274f74155a37bd9f511636ce1
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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