Formaldehyde → HCID 11284951, compound

HRID 547827Notes

Reaction equation

HRID 547827 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[N:10]=[CH:9][C:8]([N:11]([CH3:31])[C:12](=[O:30])[C:13]([C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)([CH3:15])[CH3:14])=[C:7]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[CH3:39])[CH:6]=1.C=O.S([O-])([O-])(=O)=O.[Mg+2].[CH2:48](N(CC)CC)C.[C:55](Cl)(=[O:57])[CH3:56]>ClCCCl>[C:55]([N:1]1[CH2:2][CH2:3][N:4]([C:5]2[N:10]=[CH:9][C:8]([N:11]([CH3:31])[C:12](=[O:30])[C:13]([C:16]3[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=[C:20]([C:22]([F:24])([F:25])[F:23])[CH:21]=3)([CH3:15])[CH3:14])=[C:7]([C:32]3[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=3[CH3:39])[CH:6]=2)[CH2:48]1)(=[O:57])[CH3:56]

Participants

7

Reactant 5

HCID 712Formaldehyde2×HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 24083Sulfuric acid magnesium salt (1:1)HCID 11157180HCID 11157180, compound

Product 1

HCID 11284951HCID 11284951, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 50 mg (0.090 mmol) N-[6-(2-amino-ethylamino)-4-(4-fluoro-2-methyl-phenyl)-pyridin-3-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide in 2 ml 1,2-dichloroethane were added 3 mg (0.1 mmol) paraformaldehyde and 32 mg (0.27 mmol) magnesium sulfate. After stirring at room temperature over night another 3 mg (0.1 mmol) paraformaldehyde were added and the reaction mixture was heated to 85° C. After 1 h the reaction mixture was cooled to room temperature and treated with 14 mg (0.13 mmol) triethylamine and 11 mg (0.13 mmol) acetyl chloride. Conversion was monitored by thin layer chromatography. After complete consumption of the starting material the reaction mixture was diluted with water and extracted with three portions of dichloromethane. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 40 mg (73%) of the title compound as an off-white solid.

Workup

  1. additionwere added
  2. temperatureAfter 1 h the reaction mixture was cooled to room temperature
  3. customAfter complete consumption of the starting material the reaction mixture
  4. additionwas diluted with water
  5. extractionextracted with three portions of dichloromethane
  6. dry with materialThe combined organic layers were dried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography

Sources & evidence

ORD record
ord-2a43763833594dd19a08886c55f4e356
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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