N-(5-bromo-3,6-diethylpyrazin-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-amine → N-[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]-6,7-dihydro-5H-cyclopenta[b]pyridin-5-amine

HRID 1824167Notes

Reaction equation

HRID 1824167 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:28][CH3:29])[C:12]([NH:17][C@@H:18]2[C:26]3[C:21](=C[CH:23]=[CH:24][CH:25]=3)[CH2:20][C@@H:19]2O)=[N:13][C:14]=1[CH2:15][CH3:16].BrC1[N:32]=C(CC)C(NC2C3C(=NC=CC=3)CC2)=NC=1CC>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:28][CH3:29])[C:12]([NH:17][CH:18]2[C:26]3[C:25](=[N:32][CH:19]=[CH:20][CH:21]=3)[CH2:24][CH2:23]2)=[N:13][C:14]=1[CH2:15][CH3:16]

Participants

5

Reactant 2

HCID 22147533N-(5-bromo-3,6-diethylpyrazin-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-amineHCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 22147463N-[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]-6,7-dihydro-5H-cyclopenta[b]pyridin-5-amine

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Following the procedure for the preparation of (1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol but substituting N-(5-bromo-3,6-diethylpyrazin-2-yl)-6,7-dihydro-5H-cyclopenta[b]pyridin-5-amine, ethylene glycol dimethyl ether and tetrakis(triphenylphosphine) palladium and making non-critical variations provided the title compound as a oil: 1H NMR (400 MHz, CDCl3) δ) 8.50, 7.73, 7.51, 7.36–7.28, 7.17, 5.88, 4.67, 3.26–3.08, 2.86, 2.70, 2.51, 2.05–1.96, 1.29, 1.12; HRMS (FAB) calcd for C22H22Cl2N4+H 413.1299, found 413.1286.

Sources & evidence

ORD record
ord-9d9673cec4624d04922492d872229c40
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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