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

HRID 1824288Notes

Reaction equation

HRID 1824288 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]2OC)=NC=1CC.[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=1[C:39]1[N:40]=[C:41]([CH:58]=[CH2:59])[C:42]([NH:47][C@@H:48]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:50][C@@H:49]2[OH:57])=[N:43][C:44]=1[O:45][CH3:46]>>[Cl:31][C:32]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:33]=1[C:39]1[N:40]=[C:41]([CH:58]=[CH2:59])[C:42]([NH:47][C@@H:48]2[C:56]3[C:51](=[CH:52][CH:53]=[CH:54][CH:55]=3)[CH2:50][C@@H:49]2[O:57][CH2:2][CH3:3])=[N:43][C:44]=1[O:45][CH3:46]

Participants

3

Reactant 2

HCID 101273985-(2,4-dichlorophenyl)-3,6-diethyl-N-[(1S,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amineHCID 58631243(1R,2S)-1-{[5-(2,4-dichlorophenyl)-6-methoxy-3-vinylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 586312355-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-6-methoxy-3-vinylpyrazin-2-amine

Procedure

Following the procedure for the preparation of 5-(2,4-dichlorophenyl)-3,6-diethyl-N-[(1S,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]pyrazin-2-amine but substituting (1R,2S)-1-{[5-(2,4-dichlorophenyl)-6-methoxy-3-vinylpyrazin-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 1.11–1.14, 3.04–3.08, 3.37–3.44, 3.60–3.68, 3.84, 4.28–4.30, 5.34–5.37, 5.68–5.71, 5.90–5.99, 6.66–6.73, 7.14–7.26, 7.32–7.40; MS (ESI+) for C24H23Cl2N3O2 m/z 456 (M+H)+.

Sources & evidence

ORD record
ord-8f3d7bb5983d47fa9e32e2d5289f2b3d
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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