1-Ethynylcyclopentanol → 3-(1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)-10-((1-hydroxycyclopentyl)ethynyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

HRID 575336Notes

Reaction equation

HRID 575336 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([C:19]4[CH:20]=[N:21][N:22]([CH2:24][C:25]([OH:28])([CH3:27])[CH3:26])[CH:23]=4)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:29]=1.[C:30]([C:32]1([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33]1)#[CH:31]>>[OH:28][C:25]([CH3:27])([CH3:26])[CH2:24][N:22]1[CH:23]=[C:19]([C:13]2[N:8]3[CH:9]4[CH2:12][CH:11]([C:5]5[CH:4]=[CH:3][C:2]([C:31]#[C:30][C:32]6([OH:37])[CH2:36][CH2:35][CH2:34][CH2:33]6)=[CH:29][C:6]=5[C:7]3=[N:15][C:14]=2[C:16]([NH2:18])=[O:17])[CH2:10]4)[CH:20]=[N:21]1

Participants

3

Reactant 2

HCID 870741-EthynylcyclopentanolHCID 8669336410-bromo-3-(1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)-6,7-dihydro-5H-5,7 methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Product 1

HCID 866933703-(1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)-10-((1-hydroxycyclopentyl)ethynyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Procedure

10-bromo-3-(1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)-6,7-dihydro-5H-5,7 methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide was reacted with 1-ethynylcyclopentanol via General Procedure E to afford 20 mg (14.5%) of 3-(1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)-10-((1-hydroxycyclopentyl)ethynyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide following reverse phase purification. M+1=486.

Workup

  1. customto afford
  2. custom20 mg (14.5%) of 3-(1-(2-hydroxy-2-methylpropyl)-1H-pyrazol-4-yl)-10-((1-hydroxycyclopentyl)ethynyl)-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide following reverse phase purification

Sources & evidence

ORD record
ord-5921cab5a2ea4fb1a0da4d7fe89bc10e
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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