Diisopropylethylamine → HCID 178437657, compound

HRID 1874872Notes

Reaction equation

HRID 1874872 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:16]([Cl:17])=[CH:15][CH:14]=[C:13]([CH2:18][NH:19]C)[C:12]=2[F:21])[CH:9]=1)[C:5]#[N:6].[Cl:22][C:23]1[N:24]=[C:25]([CH2:31][CH3:32])[NH:26][C:27]=1[C:28]([OH:30])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:22][C:23]1[N:24]=[C:25]([CH2:31][CH3:32])[NH:26][C:27]=1[C:28]([NH:19][CH2:18][C:13]1[CH:14]=[CH:15][C:16]([Cl:17])=[C:11]([O:10][C:8]2[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=2)[C:12]=1[F:21])=[O:30]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59451460HCID 59451460, compoundHCID 178437661HCID 178437661, compound

Product 1

HCID 178437657HCID 178437657, compoundYield 58.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-ethyl-1H-imidazole-5-carboxamide was prepared in a similar manner as described herein from 3-chloro-5-({6-chloro-2-fluoro-3-[(methylamino)methyl]phenyl}oxy)benzonitrile (0.713 g, 2.29 mmol), 4-chloro-2-ethyl-1H-imidazole-5-carboxylic acid (0.400 g, 2.29 mmol), HATU (1.133 g, 2.98 mmol), DIPEA (0.520 mL, 2.98 mmol) and DMF (12 mL). Purification was accomplished by silica gel chromatography (0-5% MeOH (2M NH3) in CH2Cl2) to afford the title compound (0.622 g, 58%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 12.74 (s, 1H), 8.09 (br. s., 1H), 7.81-7.84 (m, 1H), 7.48-7.53 (m, 2H), 7.45-7.47 (m, 1H), 7.33-7.40 (m, 1H), 4.54 (d, 2H), 2.60 (q, 2H), 1.18 (t, 3H). ES-LCMS: m/z 467.0, 469.0 (M+H).

Workup

  1. custom4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-ethyl-1H-imidazole-5-carboxamide was prepared in a similar manner
  2. customPurification

Sources & evidence

ORD record
ord-adf1d36927804cb3b610d58d676683ac
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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