1-Ethynylcyclopentanol → HCID 71714693, compound

HRID 575182Notes

Reaction equation

HRID 575182 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:18]=1.[C:19]([C:21]1([OH:26])[CH2:25][CH2:24][CH2:23][CH2:22]1)#[CH:20]>>[OH:26][C:21]1([C:19]#[C:20][C:2]2[CH:3]=[CH:4][C:5]3[O:11][CH2:10][CH2:9][N:8]4[CH:12]=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]4[C:6]=3[CH:18]=2)[CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 870741-EthynylcyclopentanolHCID 6831288310-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

Product 1

HCID 71714693HCID 71714693, compound

Procedure

10-Bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide (0.1 g) was reacted with 1-ethynylcyclopentanol similar to as described in Procedure E to afford 22.4 mg of 10-[2-(1-hydroxycyclopentyl)ethynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide following reverse phase hplc purification. MS (Q1) 338 (M)+. 1H NMR (400 MHz, DMSO) δ 8.50 (d, J=2.1 Hz, 1H), 7.84-7.71 (m, 1H), 7.54 (d, J=23.6 Hz, 1H), 7.29 (dd, J=8.5, 2.1 Hz, 1H), 7.10 (s, 1H), 7.01 (d, J=8.5 Hz, 1H), 5.28 (s, 1H), 4.49 (d, J=12.6 Hz, 4H), 1.94-1.84 (m, 4H), 1.82-1.62 (m, 5H).

Sources & evidence

ORD record
ord-b53f5e26d73d48e2a2ad8c754f93f0cc
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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