N-(3,6-diethylpyrazin-2-yl)-6-ethyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine → N-(5-bromo-3,6-diethylpyrazin-2-yl)-6-ethyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine

HRID 1612258Notes

Reaction equation

HRID 1612258 reaction equation
[Br:1]C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.[CH2:23]([C:25]1[C:26]([NH:33][CH:34]2[C:38]3=[N:39][CH:40]=[CH:41][CH:42]=[C:37]3[CH2:36][CH:35]2[CH2:43][CH3:44])=[N:27][C:28]([CH2:31][CH3:32])=[CH:29][N:30]=1)[CH3:24]>>[Br:1][C:29]1[N:30]=[C:25]([CH2:23][CH3:24])[C:26]([NH:33][CH:34]2[C:38]3=[N:39][CH:40]=[CH:41][CH:42]=[C:37]3[CH2:36][CH:35]2[CH2:43][CH3:44])=[N:27][C:28]=1[CH2:31][CH3:32]

Participants

3

Reactant 2

HCID 22147247N-(3,6-diethylpyrazin-2-yl)-6-ethyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amineHCID 58583245(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 22147301N-(5-bromo-3,6-diethylpyrazin-2-yl)-6-ethyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine

Procedure

Following the procedure for the preparation of (1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol but substituting N-(3,6-diethylpyrazin-2-yl)-6-ethyl-6,7-dihydro-5H-cyclopenta[b]pyridin-7-amine and making non-critical variations provided the title compound as a oil: 1H NMR (400 MHz, CDCl3) δ) 8.43, 7.62, 7.19, 5.37, 5.28, 3.11, 3.08, 2.87-2.69, 1.41-1.26, 0.86; HRMS (FAB) calcd for C18H23BrN4+H 375.1185, found 375.1189.

Sources & evidence

ORD record
ord-8070fbb983754eca8d181a3581a43a6e
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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