2-Chloroethyl isocyanate → 5-[3-({[(2-chloroethyl)amino]carbonyl}amino)propyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

HRID 1717413Notes

Reaction equation

HRID 1717413 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[CH:12][CH:11]=2)[N:8]=[N:7][C:6]=1[C:21]([NH:23][CH:24]1[CH2:26][CH2:25]1)=[O:22].[Cl:27][CH2:28][CH2:29][N:30]=[C:31]=[O:32]>C1COCC1>[Cl:27][CH2:28][CH2:29][NH:30][C:31]([NH:1][CH2:2][CH2:3][CH2:4][C:5]1[N:9]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([NH:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:15]=2)[N:8]=[N:7][C:6]=1[C:21]([NH:23][CH:24]1[CH2:26][CH2:25]1)=[O:22])=[O:32]

Participants

4

Reactant 2

HCID 160352-Chloroethyl isocyanateHCID 576650915-(3-aminopropyl)-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide

Product 1

HCID 576649085-[3-({[(2-chloroethyl)amino]carbonyl}amino)propyl]-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamideYield 97.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(3-aminopropyl)-N-cyclopropyl-1-{4-[(ethylamino)carbonyl]phenyl}-1H-1,2,3-triazole-4-carboxamide (356 mg, 1 mmol) obtained in Example 1202 in THF (5 ml) was added 1-chloro-2-isocyanatoethane (106 mg, 1 mmol) at room temperature, and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration and dried to give the title compound as a white powder (450 mg, 97.4%).

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-37dcd0bddcc34c9ea4d8442645ce8e4b
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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