1,1'-Carbonyldiimidazole → 5-Amino-4-(3-{3-[(tert-butoxycarbonyl)amino]propyl}ureido)-1-methylpyrazole

HRID 1247791Notes

Reaction equation

HRID 1247791 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].[NH2:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21].C(N(C(C)C)C(C)C)C.S(=O)(=O)(O)O.[NH2:39][C:40]1[CH:41]=[N:42][N:43]([CH3:46])[C:44]=1[NH2:45]>C(Cl)Cl>[NH2:45][C:44]1[N:43]([CH3:46])[N:42]=[CH:41][C:40]=1[NH:39][C:1]([NH:13][CH2:14][CH2:15][CH2:16][NH:17][C:18]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:24])=[O:2]

Participants

6

Reactant 4

HCID 682631,1'-CarbonyldiimidazoleHCID 81531DiisopropylethylamineHCID 2735700tert-Butyl (3-aminopropyl)carbamateHCID 219045711H-Pyrazole, 4,5-diamine-1-methyl-, sulfate (1:1)

Product 1

HCID 219045935-Amino-4-(3-{3-[(tert-butoxycarbonyl)amino]propyl}ureido)-1-methylpyrazoleYield 56.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 1,1′-carbonyldiimidazole (1.94 g) in methylene chloride (20 ml) was added tert-butyl N-(3-aminopropyl)carbamate (2.30 g), and the mixture was stirred at room temperature for 1 hour. To the reaction mixture were added N-ethyldiisopropylamine (2.56 g) and 4,5-diamino-1-methylpyrazole sulfuric acid salt, (2.10 g), and the mixture was stirred at 30° C. for 3 days. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with 6% methanol/chloroform to give 5-amino-4-(3-{3-[(tert-butoxycarbonyl)amino]propyl}ureido)-1-methylpyrazole (1.75 g) as a solid.

Workup

  1. stirringthe mixture was stirred at 30° C. for 3 days
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was purified by column chromatography on silica gel eluting with 6% methanol/chloroform

Sources & evidence

ORD record
ord-2cf92ed43c854fd488a700ce5b093ce9
Source dataset
uspto-grants-2006_10
Patent number
US07129232B2

Reaction notes

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