1-Ethynylcyclobutan-1-ol → 10-[2-(1-hydroxycyclobutyl)ethynyl]-N3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide

HRID 575347Notes

Reaction equation

HRID 575347 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]([NH:20][CH3:21])=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:22]=1.[C:23]([C:25]1([OH:29])[CH2:28][CH2:27][CH2:26]1)#[CH:24]>>[OH:29][C:25]1([C:23]#[C:24][C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[C:12]([C:18]([NH:20][CH3:21])=[O:19])=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]4[C:6]=3[CH:22]=2)[CH2:28][CH2:27][CH2:26]1

Participants

3

Reactant 2

HCID 225974291-Ethynylcyclobutan-1-olHCID 8669318610-bromo-N3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide

Product 1

HCID 8669338310-[2-(1-hydroxycyclobutyl)ethynyl]-N3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamideYield 46.2%

Procedure

10-bromo-N3-methyl-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2,3-dicarboxamide was reacted with 1-ethynylcyclobutanol as described in General Procedure F without making critical modifications to afford 48 mg (46.2%) of 10-[2-(1-hydroxycyclobutyl)ethynyl]-N3-methyl-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2,3-dicarboxamide. M+1=381.2.

Sources & evidence

ORD record
ord-bd52cad39062426ba4d4edd88481798d
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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