Formamide → HCID 89754613, compound

HRID 575422Notes

Reaction equation

[Br:1][C:2]1[C:3]([F:34])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:20]([CH:22]4[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:23]4)[OH:21])=[C:14]([C:16]([O:18]C)=O)[N:15]=[C:7]3[C:6]=2[CH:33]=1.C[O-].[Na+].C([NH2:40])=O>>[Br:1][C:2]1[C:3]([F:34])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:20]([OH:21])[CH:22]4[CH2:25][N:24]([C:26]([O:28][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:27])[CH2:23]4)=[C:14]([C:16](=[O:18])[NH2:40])[N:15]=[C:7]3[C:6]=2[CH:33]=1

Participants

Reactant 3

HCID 713Formamide

HCID 10942334Sodium Methoxide

HCID 86693475HCID 86693475, compound

Product 1

HCID 89754613HCID 89754613, compoundYield 82%

Procedure

tert-butyl 3-((10-bromo-2-carbamoyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepin-3-yl)(hydroxy)methyl)azetidine-1-carboxylate was prepared similarly to as described in General Procedure L. Methyl 10-bromo-3-((1-(tert-butoxycarbonyl)azetidin-3-yl)(hydroxy)methyl)-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxylate was reacted with sodium methoxide and formamide to afford 160 mg (82% yield) of the title compound.

Workup

customtert-butyl 3-((10-bromo-2-carbamoyl-9-fluoro-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepin-3-yl)(hydroxy)methyl)azetidine-1-carboxylate was prepared similarly

Sources & evidence

ORD record: ord-11992dabf3b14519aea460c616d63dc0
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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