1-(Oxan-2-yl)-1H-pyrazole-5-carbaldehyde → HCID 86693468, compound

HRID 575415Notes

Reaction equation

HRID 575415 reaction equation
[Br:1][C:2]1[C:3]([F:21])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[CH:13]=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:20]=1.[O:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH:23]1[N:28]1[C:32]([CH:33]=[O:34])=[CH:31][CH:30]=[N:29]1>>[Br:1][C:2]1[C:3]([F:21])=[CH:4][C:5]2[CH:11]3[CH2:10][CH:9]([CH2:12]3)[N:8]3[C:13]([CH:33]([OH:34])[C:32]4[N:28]([CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27][O:22]5)[N:29]=[CH:30][CH:31]=4)=[C:14]([C:16]([O:18][CH3:19])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:20]=1

Participants

3

Reactant 2

HCID 31643131-(Oxan-2-yl)-1H-pyrazole-5-carbaldehydeHCID 86693079Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate

Product 1

HCID 86693468HCID 86693468, compoundYield 43%

Procedure

Methyl 10-bromo-9-fluoro-3-(hydroxy(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was prepared similarly according to the procedure in Example 9. Methyl 10-bromo-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was reacted with 2-tetrahydropyran-2-ylpyrazole-3-carbaldehyde to afford 329 mg (43% yield) of the title compound.

Workup

  1. customMethyl 10-bromo-9-fluoro-3-(hydroxy(1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-5-yl)methyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was prepared similarly

Sources & evidence

ORD record
ord-273657e64e274289b671266a624d6f23
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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