1-Hydroxybenzotriazole → HCID 86593414, compound

HRID 1247837Notes

Reaction equation

HRID 1247837 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([OH:14])[C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.S(O)(O)(=O)=O.[CH3:42][N:43]1[C:47]([NH2:48])=[C:46]([NH2:49])[CH:45]=[N:44]1.C(N(CC)C(C)C)(C)C>ClCCl.O1CCCC1>[NH2:48][C:47]1[N:43]([CH3:42])[N:44]=[CH:45][C:46]=1[NH:49][C:11](=[O:13])[CH:10]([OH:14])[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

8

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 129598503-((tert-Butoxycarbonyl)amino)-2-hydroxypropanoic acidHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 86593414HCID 86593414, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-[(tert-butoxycarbonyl)amino]-2-hydroxypropanoic acid (1.61 g) in dichloromethane (8 ml) and tetrahydrofuran (8 ml) were added HOBT (1.59 g) and WSCD HCl (3.01 g), and the mixture was stirred at room temperature for 1 hour. The solution was cooled to 0° C., and 1-methyl-1H-pyrazole-4,5-diamine sulfate and N,N-diisopropylethylamine (4.1 ml) were added. The mixture was stirred at room temperature for 8 hours. The solvent was removed under reduced pressure to give crude tert-butyl {3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-2-hydroxy-3-oxopropyl}carbamate, which was used in the next reaction without further purification.

Workup

  1. temperatureThe solution was cooled to 0° C.
  2. stirringThe mixture was stirred at room temperature for 8 hours
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0890d3f51a04476183a862a1d93cf660
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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