Formamide → 10-Bromo-9-fluoro-3-[(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575410Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:19][C:20]4[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=4)=[C:13]([C:15]([O:17]C)=O)[N:14]=[C:7]3[C:6]=2[CH:26]=1.C[O-].[Na+].C([NH2:33])=O>>[Br:1][C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([CH2:19][C:20]4[N:24]([CH3:25])[N:23]=[CH:22][CH:21]=4)=[C:13]([C:15]([NH2:33])=[O:17])[N:14]=[C:7]3[C:6]=2[CH:26]=1

Participants

Reactant 3

HCID 713Formamide

HCID 10942334Sodium Methoxide

HCID 86693460Methyl 10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate

Product 1

HCID 8669346110-Bromo-9-fluoro-3-[(2-methylpyrazol-3-yl)methyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

Procedure

10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was prepared similarly to as described in General Procedure L. Methyl 10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxylate was reacted with sodium methoxide and formamide to afford 11 mg (11% crude yield) of the crude title compound which was carried forward without further purification.

Workup

custom10-bromo-9-fluoro-3-((1-methyl-1H-pyrazol-5-yl)methyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide was prepared similarly

Sources & evidence

ORD record: ord-16e6281abb3c4e5bb3b6367d6c728942
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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