Formaldehyde → HCID 11399244, compound

HRID 547820Notes

Reaction equation

[F:1][C:2]([F:41])([F:40])[C:3]1[CH:4]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([NH:32][CH:33]([CH2:36][OH:37])[CH2:34][OH:35])=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH2:42]=O.S([O-])([O-])(=O)=O.[Mg+2]>O>[F:11][C:9]([F:12])([F:10])[C:7]1[CH:6]=[C:5]([C:13]([CH3:39])([CH3:38])[C:14]([N:16]([C:18]2[CH:19]=[N:20][C:21]([N:32]3[CH:33]([CH2:36][OH:37])[CH2:34][O:35][CH2:42]3)=[CH:22][C:23]=2[C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=2[CH3:31])[CH3:17])=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:40])[F:41])[CH:8]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 0.10 g (0.17 mmol) 2-(3,5-bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-methyl-phenyl)-6-(2-hydroxy-1-hydroxymethyl-ethylamino)-pyridin-3-yl]-N-methyl-isobutyramide (Example 142), 12 mg (0.39 mmol) paraformaldehyde and 61 mg (0.51 mmol) magnesium sulfate in 2 ml 1,2-dichloromethane was heated at 85° C. until complete consumption of starting material. After cooling to room temperature the reaction mixture was diluted with water and extracted with 3 portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 60 mg (59%) of the title compound as an off-white solid.

Workup

temperatureAfter cooling to room temperature the reaction mixture
extractionextracted with 3 portions of tert-butyl methyl ether
dry with materialThe combined organic extracts were dried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-3784e5cd2d424010a1f8510c7253c561
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939533B2

Reaction notes

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