Formaldehyde → HCID 11319727, compound

HRID 547826Notes

Reaction equation

HRID 547826 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.[CH2:40]=O.S([O-])([O-])(=O)=O.[Mg+2].C(N(CC)C(C)C)(C)C.[CH3:57][S:58](Cl)(=[O:60])=[O:59]>ClCCCl.CN(C1C=CN=CC=1)C.COC(C)(C)C>[F:23][C:22]([F:24])([F:25])[C:20]1[CH:21]=[C:16]([C:13]([CH3:15])([CH3:14])[C:12]([N:11]([C:8]2[CH:9]=[N:10][C:5]([N:4]3[CH2:3][CH2:2][N:1]([S:58]([CH3:57])(=[O:60])=[O:59])[CH2:40]3)=[CH:6][C:7]=2[C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=2[CH3:39])[CH3:31])=[O:30])[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=1

Participants

9

Reactant 5

HCID 712FormaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11157180HCID 11157180, compound

Product 1

HCID 11319727HCID 11319727, compoundYield 40%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 0.20 g (0.36 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 42 mg (0.48 mmol) paraformaldehyde and 0.13 g (1.1 mmol) magnesium sulfate. After stirring at room temperature for 18 h 0.14 g (1.1 mmol) N,N-diisopropylethylamine, 2 mg (0.02 mmol) 4-(N,N-dimethylamino)pyridine and 62 mg (0.54 mmol) methanesulfonyl chloride were added. The reaction mixture was heated to 80° C. and kept at this temperature for 4 h. After cooling to room temperature the reaction mixture was diluted with 20 ml tert-butyl methyl ether and washed with two 20-ml portions of a saturated aqueous solution of sodium carbonate. The combined organic layers were dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography to give 93 mg (40%) of the title compound as a white foam.

Workup

  1. additionwere added
  2. temperatureAfter cooling to room temperature the reaction mixture
  3. washwashed with two 20-ml portions of a saturated aqueous solution of sodium carbonate
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. custompurified by flash chromatography

Sources & evidence

ORD record
ord-441dfeacdc2c4ae1a9d1c9bd8c9284b2
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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