2,6-Difluorobenzaldehyde → HCID 57083939, compound

HRID 1457838Notes

Reaction equation

HRID 1457838 reaction equation
FC1C=CC=C(F)C=1C=O.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[C@H:19]1[CH2:21][C@H:20]1[NH2:22].[N-:23]=[C:24]=[S:25].N[C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][N:28]=1>>[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:13]=1[C@H:19]1[CH2:21][C@H:20]1[NH:22][C:24]([NH:23][C:27]1[CH:32]=[CH:31][C:30]([C:33]#[N:34])=[CH:29][N:28]=1)=[S:25]

Participants

5

Reactant 4

HCID 1362842,6-DifluorobenzaldehydeHCID 8182602-Amino-5-cyanopyridineHCID 22940391HCID 22940391, compoundHCID 178418790HCID 178418790, compound2×

Product 1

HCID 57083939HCID 57083939, compound

Procedure

2,6-Difluorobenzaldehyde (Aldrich) was converted to cis-2-(2,6-difluorophenyl)cyclopropylamine according to Example 375 (patent application WO 93/03022) and then converted to an isothiocyanate according to Example 374 (patent application WO 93/03022). This isothiocyanate was reacted with the anion of 2-amino-5-cyanopyridine to give (+,-)-N-(cis-2-(2,6-Difluorophenyl) cyclopropyl)-N'-(5-cyanopyrid-2-yl)-thiourea. 6 mg of this compound was reacted with NBS as described in Example 4 and a final purification on alumina, resulted in 0.7 mg of the title product. Rf:0.30 Silica gel eluent:diethyl ether.

Sources & evidence

ORD record
ord-0b570b1310954bc99e86ddfc79ce0806
Source dataset
uspto-grants-1998_12
Patent number
US05849769

Reaction notes

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