5-methoxy-2,3-dihydro-1H-inden-1-amine → 3,6-diethyl-N-(5-methoxy-2,3-dihydro-1H-inden-1-yl)pyrazin-2-amine

HRID 1824157Notes

Reaction equation

HRID 1824157 reaction equation
[CH2:1]([C:3]1[C:4]([NH:11][C@@H:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14][C@@H:13]2O)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2].[CH3:22][O:23]C1C=C2C(=CC=1)C(N)CC2>>[CH2:1]([C:3]1[C:4]([NH:11][CH:12]2[C:20]3[C:15](=[CH:16][C:17]([O:23][CH3:22])=[CH:18][CH:19]=3)[CH2:14][CH2:13]2)=[N:5][C:6]([CH2:9][CH3:10])=[CH:7][N:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 30167405-methoxy-2,3-dihydro-1H-inden-1-amineHCID 58583341(1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 221473863,6-diethyl-N-(5-methoxy-2,3-dihydro-1H-inden-1-yl)pyrazin-2-amine

Procedure

Following the procedure for the preparation of (1R,2S)-1-[(3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol but substituting 5-methoxyindan-1-amine and making non-critical variations provided the title compound as a oil: 1H NMR (CDCl3) δ 1.31, 1.89, 2.58, 2.67, 2.73, 2.91, 3.00, 3.83, 4.51, 5.69, 6.79, 6.85, 7.26, 7.69; 13C NMR (CDCl3) δ 11.08, 13.97, 26.04, 28.55, 30.84, 35.35, 55.79, 55.87, 110.39, 113.15, 125.21, 130.10, 137.12, 140.93, 145.91, 151.82, 153.69, 160.25; HRMS (FAB) calcd for C18H23N3O+H 298.1919, found 298.1900. Anal. Calcd for C18H23N3O: C, 72.70; H, 7.80; N, 14.13. Found: C, 72.51; H, 8.00; N, 13.82.

Sources & evidence

ORD record
ord-cd96217c239d4e2c9dc3d6c4b5028f6a
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

Loading…