methyl 3-bromo-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate → methyl 5-bromo-3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate

HRID 1612364Notes

Reaction equation

HRID 1612364 reaction equation
[Br:1]C1C(C(OC)=O)=NC(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=CN=1.[Cl:23][C:24]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:25]=1[C:31]1[C:32]([C:48]([O:50][CH3:51])=[O:49])=[N:33][C:34]([NH:37][C@@H:38]2[C:46]3[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=3)[CH2:40][C@@H:39]2[OH:47])=[CH:35][N:36]=1>>[Br:1][C:35]1[N:36]=[C:31]([C:25]2[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:24]=2[Cl:23])[C:32]([C:48]([O:50][CH3:51])=[O:49])=[N:33][C:34]=1[NH:37][C@@H:38]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][C@@H:39]1[OH:47]

Participants

3

Reactant 2

HCID 58583440methyl 3-bromo-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylateHCID 58583461methyl 3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate

Product 1

HCID 58583474methyl 5-bromo-3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate

Procedure

Following the procedure for the preparation of methyl 3-bromo-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate but substituting methyl 3-(2,4-dichlorophenyl)-6-{[(1R,2S)-2-hydroxy-2,3-dihydro-1H-inden-1-yl]amino}pyrazine-2-carboxylate and making non-critical variations provided the title compound as a solid: 1H NMR (CDCl3) δ 2.99-3.04, 3.20-3.25, 3.70, 3.99-4.08, 4.77, 5.59-5.62, 6.11, 7.24-7.38; MS (ESI+) for C21H16BrCl2N3O3 m/z 509 (M+H)+.

Sources & evidence

ORD record
ord-ea5498a27f2c485196f4852969bd167f
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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