Triethylamine → N-(3-Chloropropyl)-1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazol-2-carboxamide

HRID 499924Notes

Reaction equation

HRID 499924 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=2)=[O:9])[N:4]=[C:3]1[C:22](O)=[O:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[Cl:50][CH2:51][CH2:52][CH2:53][NH2:54].C(N(CC)CC)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:50][CH2:51][CH2:52][CH2:53][NH:54][C:22]([C:3]1[N:2]([CH3:1])[CH:6]=[C:5]([NH:7][C:8]([NH:10][C:11]2[CH:12]=[CH:13][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=2)=[O:9])[N:4]=1)=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 114690951-Propanamine, 3-chloro-, hydrochlorideHCID 594218021-Methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic Acid

Product 1

HCID 59421821N-(3-Chloropropyl)-1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazol-2-carboxamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

140 mg (0.36 mmol) of 1-methyl-4-[({[4-(trifluoromethoxy)phenyl]amino}carbonyl)amino]-1H-imidazole-2-carboxylic acid (Example 29A) are dissolved in 8 ml of DMF and, after addition of 204 mg (0.54 mmol) of HATU and 66 mg (0.54 mmol) of DMAP, stirred at room temperature for 15 minutes. Then a solution of 93 mg (0.72 mmol) of 3-chloropropan-1-amine hydrochloride and 80 mg (0.79 mmol) of triethylamine in 1 ml of DMF is added dropwise, and the reaction mixture is stirred overnight. The reaction mixture is purified by preparative HPLC. The product-containing fractions are evaporated in vacuo.

Workup

  1. stirringthe reaction mixture is stirred overnight
  2. customThe reaction mixture is purified by preparative HPLC
  3. customThe product-containing fractions are evaporated in vacuo

Sources & evidence

ORD record
ord-3a64e892f1424da095ebd32ff4b7a49d
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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