(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-yl acetate → methyl 6-{[(1R,2S)-2-(acetyloxy)-2,3-dihydro-1H-inden-1-yl]amino}-3-(2,4-dichlorophenyl)-5-methoxypyrazine-2-carboxylate

HRID 1612367Notes

Reaction equation

C(O[C@H]1CC2C(=CC=CC=2)[C@H]1NC1C(CC)=NC(C2C=CC(Cl)=CC=2Cl)=C(CC)N=1)(=[O:3])C.[Cl:33][C:34]1[CH:39]=[C:38]([Cl:40])[CH:37]=[CH:36][C:35]=1[C:41]1[C:42]([C:62]([O:64][CH3:65])=[O:63])=[N:43][C:44]([NH:49][C@@H:50]2[C:58]3[C:53](=[CH:54][CH:55]=[CH:56][CH:57]=3)[CH2:52][C@@H:51]2[O:59][CH2:60][CH3:61])=[C:45]([O:47][CH3:48])[N:46]=1>>[C:60]([O:59][C@H:51]1[CH2:52][C:53]2[C:58](=[CH:57][CH:56]=[CH:55][CH:54]=2)[C@H:50]1[NH:49][C:44]1[N:43]=[C:42]([C:62]([O:64][CH3:65])=[O:63])[C:41]([C:35]2[CH:36]=[CH:37][C:38]([Cl:40])=[CH:39][C:34]=2[Cl:33])=[N:46][C:45]=1[O:47][CH3:48])(=[O:3])[CH3:61]

Participants

Reactant 2

HCID 10288660(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-yl acetate

HCID 58583266methyl 3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]amino}-5-methoxypyrazine-2-carboxylate

Product 1

HCID 58583249methyl 6-{[(1R,2S)-2-(acetyloxy)-2,3-dihydro-1H-inden-1-yl]amino}-3-(2,4-dichlorophenyl)-5-methoxypyrazine-2-carboxylate

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-yl acetate but substituting methyl 3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]amino}-5-methoxypyrazine-2-carboxylate and making non-critical variations provided the title compound as a solid: 1H NMR (CDCl3) δ 2.03, 3.10-3.143.31-3.36, 3.75, 4.05, 5.68-5.77, 6.07-6.11, 7.31-7.48; MS (ESI+) for C24H21Cl2N3O5 m/z 502 (M+H)+.

Sources & evidence

ORD record: ord-fa98d0c98af7407e9e8c3e03b9843e60
Source dataset: uspto-grants-2006_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06992087B2

Reaction notes

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