Water → tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoyl)amino]ethyl}carbamate

HRID 1247836Notes

Reaction equation

HRID 1247836 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:33])[CH2:29][C:30](O)=[O:31])[CH:4]=[N:3]1.[NH2:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:43])([CH3:42])[CH3:41].CCN=C=NCCCN(C)C.Cl.O>O1CCCC1.ClCCl>[CH3:1][N:2]1[C:6]([NH:7][C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:5]([NH:27][C:28](=[O:33])[CH2:29][C:30]([NH:34][CH2:35][CH2:36][NH:37][C:38](=[O:44])[O:39][C:40]([CH3:42])([CH3:41])[CH3:43])=[O:31])[CH:4]=[N:3]1

Participants

7

Reactant 4

HCID 962WaterHCID 187201N-BOC-ethylenediamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 219045813-{[1-Methyl-5-(tritylamino)pyrazol-4-yl]amino}-3-oxopropanoic acid

Product 1

HCID 86593413tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoyl)amino]ethyl}carbamateYield 67.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoic acid (600 mg) and tert-butyl (2-aminoethyl)carbamate (240 mg) in tetrahydrofuran (12 ml) and dichloromethane (6 ml) was added WSCD HCl (522 mg), and the whole mixture was stirred at room temperature overnight. To the reaction mixture was added water (3 ml), and the whole mixture was extracted with ethyl acetate. The extract was washed with water and brine and dried over magnesium sulfate. The evaporation of the solvent gave a crude residue, which was triturated with diisopropyl ether-ethyl acetate (2:1) to give tert-butyl {2-[(3-{[1-methyl-5-(tritylamino)-1H-pyrazol-4-yl]amino}-3-oxopropanoyl)amino]ethyl}carbamate (537 mg).

Workup

  1. extractionthe whole mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe evaporation of the solvent
  5. customgave a crude residue, which
  6. customwas triturated with diisopropyl ether-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-688ce4ad7e31499a833efcb9804b3066
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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