10-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide → 10-[(7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl)ethynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575095Notes

Reaction equation

HRID 575095 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:30])[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[CH2:23][CH2:22]1)#[CH:20]>>[OH:30][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)[C:25]2=[N:26][CH:27]=[CH:28][CH:29]=[C:24]2[CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 6831288310-Bromo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 866695787-ethynyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol

Product 1

HCID 7171545010-[(7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-7-yl)ethynyl]-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

Procedure

The title compound was prepared similarly according to Procedure E by reacting 10-bromo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide with 7-ethynyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-ol. 1H NMR (500 MHz, DMSO) δ 2.30-2.43 (1H, m), 2.54-2.61 (1H, m), 2.83-2.95 (1H, m), 2.96-3.07 (1H, m), 4.49 (4H, s), 6.21 (1H, br. s.), 7.03 (1H, d, J=8.51 Hz), 7.14 (1H, br. s.), 7.24-7.36 (2H, m), 7.57 (1H, br. s.), 7.73 (1H, d, J=7.41 Hz), 7.80 (1H, s), 8.46 (1H, d, J=4.26 Hz), 8.53 (1H, d, J=2.05 Hz); LC-MS: m/z=387.10 (M+H)+.

Sources & evidence

ORD record
ord-26d264d14313428eba2a2b01d63e1281
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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