Diisopropylethylamine → HCID 178432870, compound

HRID 1875059Notes

Reaction equation

HRID 1875059 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH2:9])=[C:4]([F:10])[C:3]=1[O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[Cl:18][C:19]1[N:20]=[C:21]([CH3:27])[NH:22][C:23]=1[C:24](O)=[O:25].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:18][C:19]1[N:20]=[C:21]([CH3:27])[NH:22][C:23]=1[C:24]([NH:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:4]=1[F:10])=[O:25]

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 68487185HCID 68487185, compoundHCID 178432882HCID 178432882, compound

Product 1

HCID 178432870HCID 178432870, compoundYield 23.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of {[4-chloro-2-fluoro-3-(phenyloxy)phenyl]methyl}amine (0.021 g, 0.083 mmol), 4-chloro-2-methyl-1H-imidazole-5-carboxylic acid (0.013 g, 0.083 mmol), HATU (0.038 g, 0.100 mmol) and DIPEA (0.017 mL, 0.100 mmol) in DMF (1 mL) was stirred at room temperature overnight. The crude reaction mixture was purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA). The fractions containing product were lyophilized to give 4-chloro-N-{[4-chloro-2-fluoro-3-(phenyloxy)phenyl]methyl}-2-methyl-1H-imidazole-5-carboxamide (0.0077 g, 18%) (trifluoroacetate salt) as a white solid. 1H NMR (400 MHz, DMSO-d6) d ppm 8.05-8.18 (m, 1H), 7.41-7.48 (m, 1H), 7.34 (t, 2H), 7.27 (t, 1H), 7.08 (t, 1H), 6.87 (d, 2 H), 4.49 (d, 2H), 2.24 (s, 3H). ES MS: m/z 394 (M+1).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by reverse phase HPLC (acetonitrile:water with 0.1% TFA)
  3. additionThe fractions containing product

Sources & evidence

ORD record
ord-1883dbd939fe47ce926385c2ca21ff79
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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