Methyl iodide → 5-(2,4-dichlorophenyl)-N-[(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]-3,6-dimethylpyrazin-2-amine

HRID 1612224Notes

Reaction equation

HRID 1612224 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]([CH2:30]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]2[O:27][CH2:28]C)=[N:13][C:14]=1[CH2:15]C.ClC1C=C(Cl)C=CC=1C1N=C(C)C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC=1C.CI>>[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]([CH3:30])[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]2[O:27][CH3:28])=[N:13][C:14]=1[CH3:15]

Participants

4

Reactant 3

HCID 6328Methyl iodideHCID 102170735-(2,4-dichlorophenyl)-N-[(1R,2S)-2-ethoxy-2,3-dihydro-1H-inden-1-yl]-3,6-diethylpyrazin-2-amineHCID 58583511HCID 58583511, compound

Product 1

HCID 103099125-(2,4-dichlorophenyl)-N-[(1R,2S)-2-methoxy-2,3-dihydro-1H-inden-1-yl]-3,6-dimethylpyrazin-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,2S)-1-{[5-(2,4-dichlorophenyl)-3,6-dimethylpyrazin-2-yl]amino}-2,3-dihydro-1H-inden-2-ol and methyl iodide, and making non-critical variations provided the title compound as a oil: 1H NMR (300 MHz, CDCl3) δ) 7.51, 7.43, 7.37-7.25, 5.86, 5.40, 4.28, 3.43, 3.23, 3.06, 2.42, 2.25; HRMS (FAB) calcd for C22H21Cl2N3O+H 414.1140, found 414.1143.

Sources & evidence

ORD record
ord-6b58b0518b6749a1b84ca1479acc45ef
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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