1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → tert-butyl (2-{[(tert-butoxycarbonyl)amino]methyl}-3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino]-3-oxopropyl)carbamate

HRID 459625Notes

Reaction equation

HRID 459625 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC.[CH3:45][N:46]1[C:50]([NH:51][C:52]([C:65]2[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=2)([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)=[C:49]([NH2:71])[CH:48]=[N:47]1>C(Cl)Cl.O>[C:19]([O:18][C:16]([NH:15][CH2:14][CH:10]([C:11]([NH:71][C:49]1[CH:48]=[N:47][N:46]([CH3:45])[C:50]=1[NH:51][C:52]([C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)([C:65]1[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=1)[C:59]1[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=1)=[O:13])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 222513823-{[(Tert-butoxy)carbonyl]amino}-2-({[(tert-butoxy)carbonyl]amino}methyl)propanoic acidHCID 685167251-methyl-N5-trityl-1H-pyrazole-4,5-diamineHCID 178418300HCID 178418300, compound

Product 1

HCID 86597881tert-butyl (2-{[(tert-butoxycarbonyl)amino]methyl}-3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino]-3-oxopropyl)carbamateYield 27.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-[(tert-butoxycarbonyl)amino]-2-{[(tert-butoxycarbonyl)amino]methyl}propanoic acid (476 mg) in methylene chloride (6 ml) were added hydroxybenzotriazole (222 mg) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (573 mg), and the mixture was stirred for 10 minutes. 1-Methyl-N5-trityl-1H-pyrazole-4,5-diamine (530 mg) was added to the above mixture, and the whole mixture was stirred at room temperature for 1 hour. Water was added to the mixture and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give tert-butyl (2-{[(tert-butoxycarbonyl)amino]methyl}-3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropyl)carbamate (270 mg).

Workup

  1. stirringthe whole mixture was stirred at room temperature for 1 hour
  2. extractionthe whole mixture was extracted with ethyl acetate
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-db57c56523bf474b97fe5e6c17c26f3e
Source dataset
uspto-grants-2007_03
Patent number
US07192943B2

Reaction notes

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