5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine → 3,6-dicyclopropyl-5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine

HRID 1824259Notes

Reaction equation

HRID 1824259 reaction equation
Cl[C:2]1C=C(Cl)C=C[C:3]=1C1N=C(CC)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2OCC)=NC=1CC.[CH:32]1([C:35]2[C:36]([NH:52][C@@H:53]3[C:61]4[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=4)[CH2:55][C@@H:54]3[OH:62])=[N:37][C:38]([CH:49]3[CH2:51][CH2:50]3)=[C:39]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=3[Cl:48])[N:40]=2)[CH2:34][CH2:33]1>>[CH:32]1([C:35]2[C:36]([NH:52][C@@H:53]3[C:61]4[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=4)[CH2:55][C@@H:54]3[O:62][CH2:2][CH3:3])=[N:37][C:38]([CH:49]3[CH2:50][CH2:51]3)=[C:39]([C:41]3[CH:46]=[CH:45][C:44]([Cl:47])=[CH:43][C:42]=3[Cl:48])[N:40]=2)[CH2:33][CH2:34]1

Participants

3

Reactant 2

HCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amineHCID 58583473(1R,2S)-1-{[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 585834203,6-dicyclopropyl-5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine

Procedure

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amine but substituting (1R,2 S)-1-{[3,6-dicyclopropyl-5-(2,4-dichlorophenyl)pyrazin-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 0.80–1.07, 1.17–1.20, 1.67, 1.79, 3.14–3.20, 3.46–3.50, 3.70–3.72, 4.35, 5.72, 5.97, 7.24–7.50; MS (ESI+) for C27H27Cl2N3O m/z 480 (M+H)+.

Sources & evidence

ORD record
ord-c8e0acacaa054799868c60b5af195d59
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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