1-methyl-1H-pyrazole-5-carbaldehyde → Methyl 10-bromo-9-fluoro-3-[hydroxy-(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benz oxazepine-2-carboxylate

HRID 575377Notes

Reaction equation

HRID 575377 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:19]=1.[CH3:21][N:22]1[C:26]([CH:27]=[O:28])=[CH:25][CH:24]=[N:23]1>>[Br:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH:27]([OH:28])[C:26]4[N:22]([CH3:21])[N:23]=[CH:24][CH:25]=4)=[C:13]([C:15]([O:17][CH3:18])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:19]=1

Participants

3

Reactant 2

HCID 70194141-methyl-1H-pyrazole-5-carbaldehydeHCID 86693131Methyl 10-bromo-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate

Product 1

HCID 86693425Methyl 10-bromo-9-fluoro-3-[hydroxy-(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benz oxazepine-2-carboxylateYield 33%

Procedure

Methyl 10-bromo-9-fluoro-3-(hydroxy(1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate was prepared similarly according to the procedure in Example 9. Methyl 10-bromo-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxylate was reacted with 1-methylpyrazole-5-carbaldehyde to afford 219 mg (33% yield) of the title compound.

Workup

  1. customMethyl 10-bromo-9-fluoro-3-(hydroxy(1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate was prepared similarly

Sources & evidence

ORD record
ord-ae7b74db20b5439997e6ec46befb78e2
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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