(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol → (1R,2S)-1-{[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

HRID 1612339Notes

Reaction equation

HRID 1612339 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1CC.Br[C:31]1[N:32]=[C:33]([CH:51]2[CH2:53][CH2:52]2)[C:34]([NH:40][C@H:41]2[C:49]3[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=3)[CH2:43][C@@H:42]2[OH:50])=[N:35][C:36]=1[CH:37]1[CH2:39][CH2:38]1>>[CH:51]1([C:33]2[C:34]([NH:40][C@@H:41]3[C:49]4[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=4)[CH2:43][C@@H:42]3[OH:50])=[N:35][C:36]([CH:37]3[CH2:39][CH2:38]3)=[C:31]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=3[Cl:8])[N:32]=2)[CH2:53][CH2:52]1

Participants

3

Reactant 2

HCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-olHCID 86588883(1S,2S)-1-[(5-bromo-3,6-dicyclopropylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 58583473(1R,2S)-1-{[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

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 (1S,2S)-1-[(5-bromo-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 0.85-0.99, 1.67, 1.82, 2.48, 3.10-3.13, 3.27-3.28, 4.79, 5.40, 5.42, 7.30-7.51; MS (ESI+) for C25H23Cl2N3O m/z 452 (M+H)+.

Sources & evidence

ORD record
ord-4297adcf596842d7b5b5751e4037ed39
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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