2-Chloroethylamine → HCID 59421926, compound

HRID 499908Notes

Reaction equation

HRID 499908 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[N:13]=[C:14]([C:28](O)=[O:29])[N:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)[CH:16]=2)=[O:10])=[C:4]([CH3:31])[CH:3]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:56][CH2:57][CH2:58][NH2:59].C(N(CC)C(C)C)(C)C>CN(C=O)C.CN(C1C=CN=CC=1)C>[Cl:56][CH2:57][CH2:58][NH:59][C:28]([C:14]1[N:15]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([C:24]([F:25])([F:27])[F:26])=[CH:22][CH:23]=2)[CH:16]=[C:12]([NH:11][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[CH3:31])=[O:10])[N:13]=1)=[O:29]

Participants

7

Reactant 4

HCID 133692-ChloroethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59421809HCID 59421809, compound

Product 1

HCID 59421926HCID 59421926, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

90.6 mg (0.2 mmol) of 4-({[(4-chloro-2-methylphenyl)amino]carbonyl}amino)-1-[4-(trifluoromethyl)benzyl]-1H-imidazole-2-carboxylic acid (Example 20A) are dissolved in 500 μl of DMF, and 36.65 mg (0.3 mmol) of DMAP and 114 mg (0.3 mmol) of HATU are added. After stirring at RT for 5 minutes, a solution of 46.4 mg (0.4 mmol) of 1-chloro-2-aminoethane and 25.8 mg (0.2 mmol) of N,N-diisopropylethylamine in 500 μl of DMF is added dropwise. The reaction mixture is stirred at RT for 6 h, then filtered and purified by preparative HPLC (method 9). The product-containing fractions are evaporated in vacuo.

Workup

  1. stirringThe reaction mixture is stirred at RT for 6 h
  2. filtrationfiltered
  3. custompurified by preparative HPLC (method 9)
  4. customThe product-containing fractions are evaporated in vacuo

Sources & evidence

ORD record
ord-657f8df468f0442c8ad9ddc4a84601e2
Source dataset
uspto-grants-2010_08
Patent number
US07767704B2

Reaction notes

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