5-bromo-N-(2,3-dihydro-1H-inden-1-yl)-3,6-dimethylpyrazin-2-amine → 5-(2,4-dichlorophenyl)-N-(2,3-dihydro-1H-inden-1-yl)-3,6-dimethylpyrazin-2-amine

HRID 1612141Notes

Reaction equation

HRID 1612141 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH2:28]C)[C:12]([NH:17][C@@H:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][C@@H:19]2O)=[N:13][C:14]=1[CH2:15]C.BrC1N=C(C)C(NC2C3C(=CC=CC=3)CC2)=NC=1C>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([CH3:28])[C:12]([NH:17][CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:20][CH2:19]2)=[N:13][C:14]=1[CH3:15]

Participants

3

Reactant 2

HCID 221474215-bromo-N-(2,3-dihydro-1H-inden-1-yl)-3,6-dimethylpyrazin-2-amineHCID 58583246(1R,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-diethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 221474205-(2,4-dichlorophenyl)-N-(2,3-dihydro-1H-inden-1-yl)-3,6-dimethylpyrazin-2-amine

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 5-bromo-N-(2,3-dihydro-1H-inden-1-yl)-3,6-dimethylpyrazin-2-amine and making non-critical variations provided the title compound as a oil: 1H NMR (CDCl3) δ 1.94, 2.29, 2.39, 2.80, 2.96, 3.08, 4.64, 5.83, 7.33, 7.51; MS (ESI+) for C21H19Cl2N3 m/z 385.30 (M+H)+.

Sources & evidence

ORD record
ord-49e1e9091023427a851f605c22637530
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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