Formaldehyde → HCID 24785631, compound

HRID 2244376Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH:28]3[CH2:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[C:11]([C:13]2[C:18]([NH2:19])=[CH:17][CH:16]=[C:15]([CH3:20])[N:14]=2)=[O:12])=[CH:4][CH:3]=1.[CH2:32]=O.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][N:10]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH:28]3[CH2:31][CH2:30][CH2:29]3)=[CH:26][CH:27]=2)[C:11]([C:13]2[C:18]([NH:19][CH3:32])=[CH:17][CH:16]=[C:15]([CH3:20])[N:14]=2)=[O:12])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 3-amino-6-methyl-pyridine-2-carboxylic acid [2-(4-chloro-phenyl)-ethyl]-(4-cyclobutyl-benzyl)-amide (151 mg, 0.348 mmol), 37% aq. formaldehyde solution (0.16 mL, 2.09 mmol) and ethanol (2 mL) was stirred at 50° C. for 3 h, then after removal of volatile material by distillation, sodium borohydride (55 mg, 1.39 mmol) was added, and stirring at 50° C. was continued over 3 h. After cooling, the reaction mixture was partitioned between ethyl acetate and water, the organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced the title compound (126 mg, 81%). Colourless gum, MS (ISP) 448.3 (M+H)+.

Workup

customafter removal of volatile material
additionwas added
stirringstirring at 50° C.
waitwas continued over 3 h
temperatureAfter cooling
customthe reaction mixture was partitioned between ethyl acetate and water
washthe organic layer was washed with brine
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-ddcc6d37a2cf46a19a562768c64bd8cb
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07678818B2

Reaction notes

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