Dichloromethane → HCID 70937253, compound

HRID 1875237Notes

Reaction equation

HRID 1875237 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[Cl:5][C:6]1[N:7]=[C:8]([N:41]=P(C)(C)C)[N:9]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:10]=1[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][C:23]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[C:25]([Cl:31])[CH:24]=2)[C:16]=1[F:32])=[O:12].[C:46]([O-:49])(O)=O.[Na+].[CH2:51](Cl)Cl>>[Cl:5][C:6]1[N:7]=[C:8]([N:41]([C:46](=[O:49])[CH3:51])[C:1](=[O:3])[CH3:2])[N:9]([CH2:33][O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])[C:10]=1[C:11]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([O:22][C:23]2[CH:28]=[C:27]([C:29]#[N:30])[CH:26]=[C:25]([Cl:31])[CH:24]=2)[C:16]=1[F:32])=[O:12]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 68763036HCID 68763036, compound

Product 1

HCID 70937253HCID 70937253, compoundYield 44%

Conditions

Temperature
45 °C

Procedure

Acetyl chloride (0.10 ml, 1.41 mmol) was added to a solution of 4-chloro-N-({4-chloro-3-[(3-chloro-5-cyanophenyl)oxy]-2-fluorophenyl}methyl)-2-[(trimethyl-λ5-phosphanylidene)amino]-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxamide (0.11 g, 0.16 mmol) in CH2Cl2 (1.0 ml) and the reaction mixture was stirred at 45° C. for 1 h. Sat'd aqueous NaHCO3 was added and the aqueous layer was extracted with EtOAc. The organic layers were combined, dried (Na2SO4), filtered, concentrated and purified by silica gel chromatography (0-40% EtOAc/hexanes) to provide the title compound (0.047 g, 44%) as a clear oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.32-7.35 (m, 1H) 7.28-7.32 (m, 2H) 7.19 (t, J=6.04 Hz, 1H) 7.13 (t, J=2.01 Hz, 1H) 7.01 (s, 1H) 5.56 (s, 2H) 4.67 (d, J=6.13 Hz, 2H) 3.55-3.63 (m, 2H) 2.30 (s, 6H) 0.80-0.89 (m, 2H)-0.04 (s, 9H).

Workup

  1. extractionthe aqueous layer was extracted with EtOAc
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (0-40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4c001ef74680427c82f41e556900fc59
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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