1-Hydroxybenzotriazole → HCID 21904547, compound

HRID 1247831Notes

Reaction equation

HRID 1247831 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:10][CH2:11][C:12]([OH:14])=O)[CH3:9])=[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.[Cl-].[Na+].O>[NH2:48][C:47]1[N:43]([CH3:42])[N:44]=[CH:45][C:46]=1[NH:49][C:12](=[O:14])[CH2:11][CH2:10][N:8]([CH3:9])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27609523-(Methylamino)propanoic acid, N-BOC protectedHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 21904547HCID 21904547, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a suspension of 3-[N-(tert-butoxycarbonyl)-N-methylamino]propanoic acid (3.33 g) in dichloromethane (33 ml) and tetrahydrofuran (33 ml) were added HOBT (3.33 g) and WSC HCl (6.29 g), and the mixture was stirred for 1 hour. To the solution were added 1-methyl-1H-pyrazole-4,5-diamine sulfate (3.45 g) and N,N-diisopropylethylamine (11.4 ml). The reaction mixture was stirred at room temperature overnight. To the resulting solution was added brine and extracted with tetrahydrofuran/ethyl acetate=1/1. The extract was dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to give tert-butyl N-{3-[(5-amino-1-methyl-1H-pyrazol-4-yl)amino]-3-oxopropyl}-N-methylcarbamate as an oil (2.4 g). This product was used in the next step without further purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. extractionextracted with tetrahydrofuran/ethyl acetate=1/1
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4de9d5090f674612a1aad5e3f2c8cf00
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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