(1R,2S)-1-[(5-bromo-3,6-diethylpyrazin-2-yl)amino]-2,3-dihydro-1H-inden-2-ol → HCID 86588868, compound

HRID 1824102Notes

Reaction equation

HRID 1824102 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]2[OH:20])=[N:6][C:7]=1[CH2:8][CH3:9].[CH2:23](C1C(N[C@@H]2C3C(=CC=CC=3)CC[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[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH2:13][CH2:23][C@H:12]2[OH:20])=[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 58583495HCID 58583495, compound

Product 1

HCID 86588868HCID 86588868, compound

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)-1-[(3,6-diethylpyrazin-2-yl)amino]-1,2,3,4-tetrahydronaphthalen-2-ol and making non-critical variations provided the title compound as a oil: 1H NMR (CDCl3) δ 1.30 (m, 6H), 1.95 (m, 1H), 2.25 (m, 1H), 2.64 (dd, J=7.5, 15.1 Hz, 2H), 2.84 (dd, J=7.6, 15.2 Hz, 2H), 2.94 (m, 2H), 4.03 (m, 1H), 4.74 (d, J=6.7 Hz, 1H), 5.08 (s, 1H) 5.16 (dd, J=6.7, 7.2 Hz, 1H), 7.2 (m, 1H), 7.28 (m, 2H), 7.35 (m, 1H); MS (EI) m/z (rel. intensity) 375 (M+, 9), 359 (68), 357 (67), 230 (45), 146 (35), 129 (69), 128 (56), 118 (55), 117 (99), 115 (68), 91 (45). HRMS (FAB) calcd for C18H22BrN3O+H 376.1025, found 376.1029. Anal. Calcd for C18H22BrN3O: C, 57.45; H, 5.89; N, 11.17; Br, 21.23. Found: C, 57.61; H, 5.88; N, 10.70.

Sources & evidence

ORD record
ord-96017ceeece14b218ff6a7c5e9ccd2a8
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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