2-Bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazine → 5-(2,4-dichlorophenyl)-3,6-diethyl-N-[Cis-5-ethyl-4,5,6,7-tetrahydro-1-benzothien-4-yl]pyrazin-2-amine

HRID 1824117Notes

Reaction equation

C(C1C(N[C@@H]2C3C(=CC=CC=3)C[C@@H]2O)=NC(CC)=CN=1)C.[CH2:22]([C@@H:24]1[C@H:32]([NH2:33])[C:28]2[CH:29]=[CH:30][S:31][C:27]=2[CH2:26][CH2:25]1)[CH3:23].Br[C:35]1[C:40]([CH2:41][CH3:42])=[N:39][C:38]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][C:44]=2[Cl:50])=[C:37]([CH2:51][CH3:52])[N:36]=1>>[Cl:50][C:44]1[CH:45]=[C:46]([Cl:49])[CH:47]=[CH:48][C:43]=1[C:38]1[N:39]=[C:40]([CH2:41][CH3:42])[C:35]([NH:33][C@@H:32]2[C:28]3[CH:29]=[CH:30][S:31][C:27]=3[CH2:26][CH2:25][C@@H:24]2[CH2:22][CH3:23])=[N:36][C:37]=1[CH2:51][CH3:52]

Participants

Reactant 3

HCID 221474372-Bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazine

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

HCID 69664645cis-5-Ethyl-4,5,6,7-tetrahydro 1-benzothiophen-4-amine

Product 1

HCID 585834445-(2,4-dichlorophenyl)-3,6-diethyl-N-[Cis-5-ethyl-4,5,6,7-tetrahydro-1-benzothien-4-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 cis-5-ethyl-4,5,6,7-tetrahydro-1-benzothiophen-4-amine and 2-bromo-5-(2,4-dichlorophenyl)-3,6-diethylpyrazine and making non-critical variations provided the title compound as a oil: 1H NMR (400 MHz, CDCl3) δ; 7.50, 7.32, 7.08, 6.98, 5.77, 4.42, 2.99, 2.95, 2.62, 2.50, 1.98, 1.73, 1.39–1.18, 1.00; HRMS (FAB) calcd for C24H27Cl2N3S+H 460.1381, found 460.1376.

Sources & evidence

ORD record: ord-0876bb6a8cb2416d89a6d3a39460d93a
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07041672B2

Reaction notes

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