N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine → 5-bromo-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine

HRID 1612208Notes

Reaction equation

HRID 1612208 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([CH2:21][CH3:22])[C:5]([NH:10][C@@H:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][C@@H:12]2O)=[N:6][C:7]=1[CH2:8][CH3:9].[O:23]1C2C(=CC=CC=2)C(NC2C(CC)=NC=C(CC)N=2)CC1>>[Br:1][C:2]1[N:3]=[C:4]([CH2:21][CH3:22])[C:5]([NH:10][CH:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[O:23][CH2:13][CH2:12]2)=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 22147228N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amineHCID 58583245(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol

Product 1

HCID 221472675-bromo-N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine

Procedure

Following the procedure for the preparation of (1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol but substituting N-(3,4-dihydro-2H-chromen-4-yl)-3,6-diethylpyrazin-2-amine and making non-critical variations provided the title compound as a oil: 1H NMR (300 MHz, CDCl3) δ) 7.28-7.21, 6.96-6.89, 5.26, 4.54, 4.29-4.22, 2.84, 2.57, 2.22, 1.32-1.24; HRMS (FAB) calcd for C17H20BrN3O+H 362.0868, found 362.0861. Anal. Calcd for C17H20BrN3O: C, 56.36; H, 5.56; N, 11.60. Found: C, 56.10; H, 5.56; N, 11.35.

Sources & evidence

ORD record
ord-d40185f8c04544eebb698337aa4895cb
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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