(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol → (1S,2S)-1-[(5-bromo-3,6-dicyclopropylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

HRID 1824249Notes

Reaction equation

HRID 1824249 reaction equation
[Br:1]C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.[CH:23]1([C:26]2[C:27]([NH:35][C@@H:36]3[C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH2:38][C@@H:37]3[OH:45])=[N:28][C:29]([CH:32]3[CH2:34][CH2:33]3)=[CH:30][N:31]=2)[CH2:25][CH2:24]1>>[Br:1][C:30]1[N:31]=[C:26]([CH:23]2[CH2:24][CH2:25]2)[C:27]([NH:35][C@H:36]2[C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38][C@@H:37]2[OH:45])=[N:28][C:29]=1[CH:32]1[CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 58583245(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-olHCID 58583389(1R,2S)-1-[(3,6-dicyclopropylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 86588883(1S,2S)-1-[(5-bromo-3,6-dicyclopropylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

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 (1R,2S)-1-[(3,6-dicyclopropylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol and making non-critical variations provided the title compound as a solid: 1H NMR (CDCl3) δ 0.89–1.03, 1.27–1.30, 1.71–1.75, 2.36–2.39, 3.05–3.09, 3.25–3.30, 4.72–4.75, 5.45–5.46, 7.26–7.33; MS (ESI+) for C19H20BrN3O m/z 386 (M+H)+.

Sources & evidence

ORD record
ord-776dbb532d754159a94b86fceb7c421f
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

Loading…