(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol → cis-(+/-)-4-[(5-Bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol

HRID 1824223Notes

Reaction equation

HRID 1824223 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]3C(=CC=C[CH:18]=3)C[C@@H:12]2[OH:20])=[N:6][C:7]=1[CH2:8][CH3:9].C(C1C(N[C@@H]2C[O:37]C[C@H]2O)=NC(CC)=CN=1)C>>[Br:1][C:2]1[N:3]=[C:4]([CH2:21][CH3:22])[C:5]([NH:10][C@H:11]2[CH2:12][O:20][CH2:18][C@H:19]2[OH:37])=[N:6][C:7]=1[CH2:8][CH3:9]

Participants

3

Reactant 2

HCID 58583245(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-olHCID 86588871trans-(+/-)-4-[(3,6-Diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol

Product 1

HCID 86588877cis-(+/-)-4-[(5-Bromo-3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol

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 trans-(+/−)-4-[(3,6-diethylpyrazin-2-yl)amino]tetrahydrofuran-3-ol and making non-critical variations provided the title compound as a light yellow solid. IR (diffuse reflectance) 3398, 2971, 2938, 1569, 1539, 1490, 1466, 1447, 1413, 1397, 1251, 1232, 1054, 969, 891 cm−1; OAMS supporting ions at: ESI+ 315.9 & ESI− 313.9; MS (EI) m/z 315 (M+); HRMS (FAB) calcd for C12H18BRN3O2+H1 316.0661, found 316.0656; Anal. Calcd for C12H18BrN3O2: C, 45.58; H, 5.74; N, 13.29. Found: C, 45.49; H, 5.84; N, 13.14.

Sources & evidence

ORD record
ord-dc7144e38cf04037a665afaa8b9d17cb
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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